WO2013017559A1 - N-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamides and use thereof as herbicides - Google Patents

N-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamides and use thereof as herbicides Download PDF

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Publication number
WO2013017559A1
WO2013017559A1 PCT/EP2012/064863 EP2012064863W WO2013017559A1 WO 2013017559 A1 WO2013017559 A1 WO 2013017559A1 EP 2012064863 W EP2012064863 W EP 2012064863W WO 2013017559 A1 WO2013017559 A1 WO 2013017559A1
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alkyl
heterocyclyl
cycloalkyl
heteroaryl
cor
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PCT/EP2012/064863
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German (de)
French (fr)
Inventor
Ralf Braun
Simon DÖRNER-RIEPING
Arnim Köhn
Hartmut Ahrens
Stefan Lehr
Andreas Van Almsick
Isolde HÄUSER-HAHN
Hansjörg Dietrich
Elmar Gatzweiler
Ines Heinemann
Christopher Hugh Rosinger
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Bayer Intellectual Property Gmbh
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Priority to ES12745447.8T priority Critical patent/ES2542681T3/en
Priority to JP2014523298A priority patent/JP6078065B2/en
Priority to BR112014002191A priority patent/BR112014002191B1/en
Priority to US14/233,298 priority patent/US8822378B2/en
Priority to EP20120745447 priority patent/EP2739611B1/en
Priority to IN176DEN2014 priority patent/IN2014DN00176A/en
Priority to CN201280038161.9A priority patent/CN103717581B/en
Priority to PL12745447T priority patent/PL2739611T3/en
Publication of WO2013017559A1 publication Critical patent/WO2013017559A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
  • N- (tetrazol-5-yl) - and N- (triazol-5-yl) benzamides and their pharmacological activity are known. From the earlier priority, not pre-published EP101748937 certain N- (tetrazol-5-yl) - and N- (triazol-5-yl) benzamides and nicotinamides are known as herbicides. It has now been found that (tetrazole-5-yl) - and N- (triazol-5-yl) arylcarbonklareamide and
  • nicotinamides which carry special substituents in the 1-position of the tetrazole or triazole ring, are particularly suitable as herbicides.
  • An object of the present invention are thus N- (tetrazol-5-yl) - and N- (triazol-5-yl) arylcarbonklareamide of formula (I) or salts thereof
  • A is N or CY
  • B is N or CH
  • X is nitro, halogen, cyano, formyl, thiocyanato, (Ci-C6) alkyl, halo (Ci- C6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl , (C2-C6) alkynyl, halo (C 3 -C 6) - alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O) N
  • Z represents halogen, cyano, rhodano, halo (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogeno (C 2 -C 6 ) -alkynyl, -C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, halo (C 3 - C 6 ) - cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O)
  • R is CH 2 R 6 ,
  • Cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each substituted by s substituents selected from the group consisting of methyl, ethyl, methoxy, cyano, nitro, trifluoromethyl and halo, and wherein Heterocyclyl and cycloalkyl carry n oxo groups,
  • Q is O, S or NR 3 ,
  • R 1 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O - (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) - alkyl heteroaryl, Heterocycl, (Ci-C 6) alkyl-heterocycl
  • R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) - Cycloalkyl- (C 1 -C 6 ) -alkyl,
  • R 4 is (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkynyl, (C3-C6) -cycloalkyl or (C3-C6) -cycloalkyl- ( C 1 -C 6 ) -alkyl,
  • R 5 is (C 1 -C 4 ) -alkyl
  • R 6 is OCOOR 4 , NR 4 COOR 4 , S (O) n - (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -haloalkyl, nitro, cyano, SiR 5 3, PO (OR 5 ) 2 , heterocyclyl or cycloalkyl, where the last two radicals m bear oxo or hydroxy groups, m is 1 or 2,
  • n 0, 1 or 2
  • s 0, 1, 2 or 3
  • t 1, 2, 3 or 4
  • alkyl radicals having more than two carbon atoms may be straight-chain or branched.
  • Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl.
  • alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl,
  • Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl.
  • the multiple bond can each be in any position of the unsaturated radical.
  • Cycloalkyl means a carbocyclic saturated ring system having three to six C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, e.g. Cyclopropenyl, cyclobutenyl,
  • Cyclopentenyl and cyclohexenyl, wherein the double bond may be in any position.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Heterocyclyl means a saturated, partially saturated or fully unsaturated cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group oxygen, nitrogen and sulfur, and additionally by a
  • heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl.
  • Heteroaryl means an aromatic cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group consisting of oxygen, nitrogen and sulfur, and may additionally be fused by a benzo ring.
  • heteroaryl stands for
  • Benzimidazol-2-yl furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1, 2,3-oxadiazolyl, 1, 2,4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1, 3,4-oxadiazolyl, 1, 2,4-triazolyl, 1, 2,3-triazolyl, 1, 2,5-triazolyl, 1, 3,4-triazolyl, 1, 2,4-triazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,3-thiadiazolyl, 1, 2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1 H-1, 2,
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, then enantiomers and
  • stereoisomers can be prepared by using stereoselective reactions using optically active starting materials and / or
  • the invention also relates to all stereoisomers and mixtures thereof, which are of the general formula (I) but are not specifically defined.
  • A is N or CY
  • B is N or CH
  • X is nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C 2 -C 4 ) -alkenyl -C 6) alkynyl, halo (C3-C6) -alkynyl, (C 3 - C 6) cycloalkyl, halo (C3-C6) cycloalkyl, Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, halo (C3-C6) cycloalkyl- (Ci-C 6) alkyl, COR 1, OR 1 , OCOR 1 ,
  • Y is hydrogen, nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, or halogen- (C 2 -C 6 ) -alkenyl , (C 2 -C 6 ) -alkynyl, halogeno (C 3 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, halogeno (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl, C 6 ) -cycloalkyl, C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno (C 3 -
  • Heterocyclyl where the six last-mentioned radicals each substituted by s radicals selected from the group halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, S (O) n - (Ci-C 6) -alkyl, (Ci-Ce) alkoxy, halo (Ci-C 6) alkoxy, (Ci-C6) - alkoxy- (Ci-C4) - substituted alkyl and cyanomethyl, and wherein heterocyclyl n carries oxo groups,
  • Z represents halogen, cyano, thiocyanato, halo (Ci-C6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halogen - (C 3 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, halogeno (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno- (C 3 -C 6 ) -alkyl C 3 -C 6) - cycloalkyl- (Ci-C 6) alkyl, COR 1, COOR 1, C (O) N (R 1) 2, C (O) NR 1 OR 1, OSO 2 R 2, S (O) n R 2 , SO 2 OR 1
  • Z can also be hydrogen, (C 1 -C 6) -alkyl or (C 1 -C 6) -alkoxy, if Y is the radical S (O) n R 2 ,
  • R is CH 2 R 6 ,
  • Cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each substituted by s substituents selected from the group consisting of methyl, ethyl, methoxy, cyano, nitro, trifluoromethyl and halo, and wherein Heterocyclyl and cycloalkyl carry n oxo groups, Q is O, S or NR 3 ,
  • R 1 represents hydrogen, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) - Alkyl-heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl-heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 4) -alkyl-
  • R 2 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 4) -alkyl C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6
  • R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl,
  • R 4 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl or (C 2 -C 6 ) -alkynyl, R 5 is methyl or ethyl, R 6 is OCOOR 4 , NR 4 COOR 4 , S (O) n - (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -haloalkyl, nitro, cyano, SiR 5 3, PO (OR 5 ) 2 or heterocyclyl, the m is oxo, m is 1 or 2,
  • n 0, 1 or 2
  • s 0, 1, 2 or 3
  • u is 1, 2, 3, 4 or 5.
  • A is N or CY
  • B is N or CH
  • X is nitro, halo, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, OR 1, S (O ) n R 2 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , (Ci -C 6) -alkyl heteroaryl, (C 1 -C 6) -alkyl heterocyclyl, where the latter two
  • Heterocyclyl carries n oxo groups
  • Y is hydrogen, nitro, halogen, cyano, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, OR 1, S (O) n R 2, SO 2 N (R 1) 2, N (R 1) 2, NR 1 SO 2 R 2, NR 1 COR 1, (Ci-C 6) alkyl-S (O) n R 2, (Ci-C 6) - alkyl-OR 1, (Ci-C 6 ) -Alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) - Alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 ) -alkyl-phenyl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C
  • Z represents halogen, cyano, halo (Ci-C 6) alkyl, (C3-C6) -cycloalkyl, S (O) n R 2, 1, 2,4-triazol-1-yl, or Z may also be Is hydrogen, methyl, methoxy or ethoxy, if Y is the radical S (O) n R 2 ,
  • R is CH 2 R 6 ,
  • heterocyclyl m carries oxo groups, in each case by u radicals from the group consisting of nitro, cyano, hydroxyl, oxo, SiR 5 3 , PO (OR 5 ) 2 , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - alkoxy, halo (Ci-C 6) -alkoxy, N (R 3) 2, COR 3, OCOR 3, NR 3 COR 3, NR 3 SO 2 R 4, (C 3 -C 6) -cycloalkyl, heteroaryl, Heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl substituted (C 2 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, halo (C 2 -C 6 )
  • Q is O, S or NR 3 ,
  • R 1 represents hydrogen, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl,
  • R 2 is (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, where these three radicals mentioned above are each represented by s radicals from the group consisting of Group consisting of halogen and OR 3 are substituted,
  • R 3 is hydrogen or (C 1 -C 6 ) -alkyl, is (C 1 -C 6 ) -alkyl,
  • R 5 is methyl or ethyl
  • R 6 is OCOOR 4 , NR 4 COOR 4 , S (O) n- (C 1 -C 6 ) -alkyl, S (O) n- (C 1 -C 6 ) -haloalkyl, nitro, cyano, SiR 5 3 , PO (OR 5 ) 2 , m is 1 or 2,
  • n 0, 1 or 2
  • s 0, 1, 2 or 3
  • u is 1, 2, 3, 4 or 5.
  • benzoic acid chlorides of the formula (II) or the benzoic acids on which they are based are known in principle and can be synthesized, for example, according to the processes described in US Pat. No. 6,376,429 B1, EP 1 585 742 A1 and EP 1 202 978 A1
  • dehydrating reagents commonly used for amidation reactions such as B. 1, ⁇ -carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc . are used.
  • CDI ⁇ -carbonyldiimidazole
  • DCC dicyclohexylcarbodiimide
  • T3P 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide
  • alkylating agents such as alkyl halides, sulfonates or dialkyl sulfates can be used in the presence of a base. It may be convenient to change reaction steps in order. Thus, benzoic acids carrying a sulfoxide are not readily converted into their acid chlorides. Here it is advisable to first produce the amide on the thioether stage and then to oxidize the thioether to the sulfoxide.
  • the 5-amino-1H-tetrazoles of the formula (III) can be prepared analogously to those known from the literature
  • 5-amino-1-R-tetrazoles may be added after in Amino-tetrazole method described in Journal of the American Chemical Society (1954), 76, 923-924:
  • R is, for example, an alkyl radical.
  • 5-amino-1-R-tetrazoles can be synthesized as described in Journal of the American Chemical Society (1954) 76, 88-89:
  • the 5-amino-1H-triazoles of the formula (III) can be prepared analogously to those known from the literature
  • Aminotriazole be prepared:
  • 5-Amino-1-R-triazoles can also be synthesized, for example, as described in Chemische Berichte (1964), 97 (2), 396-404:
  • 5-amino-1-R-triazoles can also be used, for example, as in Angewandte Chemie
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • the implementation of single or multiple synthetic steps can be supported by the use of polymer-supported reagents / Scavanger resins.
  • Synthesis methods allow a number of protocols known from the literature, which in turn can be carried out manually or automatically.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • the preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of formula (I) and their salts.
  • the compounds of the formula (I) (and / or salts thereof) according to the invention have a excellent herbicidal activity against a broad spectrum of important mono- and dicotyledonous weed plants. Also difficult to control perennial harmful plants that expel from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
  • the present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, wherein one or more of the present invention
  • Compound (s) on the plants e.g., weeds such as mono- or dicotyledons
  • the compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufmaschine be applied.
  • some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
  • the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die after three to four weeks
  • Ipomoea Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus, Avena,
  • Crops such as agricultural crops or ornamental plantings.
  • the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special special traits for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • transgenic crops Preferred with respect to transgenic crops is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice and corn or even crops of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the compounds according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or
  • the application of the compounds of the invention or their salts in economically important transgenic crops of useful and ornamental plants eg.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the compounds according to the invention can preferably be employed as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant. Conventional ways of producing new plants that have modified properties compared to previously occurring plants exist
  • Glufosinate see, for example, EP-A-0242236, EP-A-242246) or glyphosate
  • transgenic crops for example cotton, with the ability
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) to produce, which the
  • transgenic crops characterized by a combination z. B. the o. G.
  • nucleic acid molecules can be used in any genetic manipulations.
  • nucleic acid molecules can be used in any genetic manipulations.
  • Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments.
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known in the art (see, for example, Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). Expression of the nucleic acid molecules can also be found in the
  • Organelles of the plant cells take place.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • transgenic plants are available, the altered properties by
  • the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against
  • Herbicides containing essential plant enzymes e.g. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydroxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD Hydroxyphenylpyruvat dioxygenases
  • Harmful plants often have effects that are specific for application in the particular transgenic culture, such as altered or specially extended weed spectrum that can be controlled
  • Expense amounts that can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of transgenic crops.
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates,
  • EC emulsifiable concentrates
  • EW emulsions
  • Water-in-oil emulsions sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG),
  • the necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are, for example
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agent, dispersing agent) in addition to the active ingredient, apart from a diluent or inert substance.
  • surfactants of the ionic and / or nonionic type wetting agent, dispersing agent
  • Formulation aids mixed.
  • Emulsifiable concentrates are made by dissolving the active ingredient in one
  • organic solvents e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • emulsifiers which may be used are: alkylarylsulfonic acid calcium salts, such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as
  • Fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,
  • Propylene oxide-ethylene oxide condensation products alkyl polyethers, sorbitan esters, e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g.
  • Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally added surfactants, such as the above with the other
  • Emulsions e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types.
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
  • Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • adhesives e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils
  • carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
  • the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. at
  • the active substance concentration can be about 1 to 90,
  • Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which
  • Granulation aids, fillers, etc. are used. In the water
  • the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%.
  • the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving,
  • Mixture formulations or in the tank mix are, for example, known active substances which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase,
  • Glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 15th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2009 and There cited literature are described. As known herbicides or
  • Plant growth regulators which can be combined with the compounds of the invention are e.g. the following active ingredients (the compounds are denoted either by the "common name” according to the International Organization for Standardization (ISO) or the chemical name or with the code number) and always include all forms of use such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • active ingredients the compounds are denoted either by the "common name” according to the International Organization for Standardization (ISO) or the chemical name or with the code number
  • ISO International Organization for Standardization
  • isomers such as stereoisomers and optical isomers.
  • One and in part also several application forms are mentioned by way of example: acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium,
  • Flufenpyr Flufenpyr-ethyl, Flumetralin, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Flumipropyn, Fluometuron, Fluorodifen,
  • Fluoroglycofen Fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate,
  • Flupyrsulfuron flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, förch lorfenuron,
  • Haloxyfop Haloxyfop-P, Haloxyfopethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop- methyl, Haloxyfop-P-methyl, Hexazinone, HW-02, d. H. 1- (dimethoxyphosphoryl) ethyl (2,4-dichlorophenoxy) acetate, imazamethabenz, imazamethabenz-n-ethyl,
  • Imazamox imazamoxammonium, imazapic, imazapyr, imazapyrisopropylammonium, imazaquin, imazaquin-amnunnonium, imazethapyr, imazethapyrammonium, imazosulfuron, inabenfide, indanofan, indaziflam, indoleacetic acid (IAA), 4-indol-3-yl-butyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, loxynil, isoparbazone, isocarbamide, isopropalin, isoproturon, isourone, isoxaben,
  • Metamifop metamitron, metazachlor, metazasulfuron, methazole, methiopyrsulfuron, methiozoline, methoxyphenones, methyldymron, 1-methylcyclopropene,
  • Methylisothiocyanate metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinates,
  • Nonanoic acid pendimethalin, pendalkin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamide, phenisopham, phenmedipham, phenmediphamethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenoputyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazoles, Profluazole, Procyazine, Prodiamine, Prifluralin, Profoxydim, Prohexadione, Prohexadione-calcium, Prohydrojasmone, Prometon, Prometry, Propachlor, Propanil, Propaquizafop, Propazine, Propam, Propisochlor, Propoxycarbazone, Propoxycarbazone-nathum, Propyrisulfuron,
  • Triafamon triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuronmethyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron , Tsitodef, Uniconazole, Uniconazole-P, Vernolate, ZJ-0862, d. H. 3,4-Dichloro-N- ⁇ 2 - [(4,6-dimethoxypyrimidin-2-yl) oxy] benzyl ⁇ aniline, and the following compounds:
  • the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dusty preparations, ground or spreading granules and sprayable
  • Compounds of the formula (I) can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
  • Table 3 Compounds according to the invention of the formula (I) in which A is N.
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
  • a readily dispersible, water-wettable powder is obtained by: 25 parts by weight of a compound of the formula (I) and / or salts thereof, 64
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight
  • Mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a
  • a water-dispersible granule is also obtained by
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
  • 1-16, 1-44, 1-60, 1-125, 1-154, 1-162, 1-163, 1-174, 1-187, 1-191, 1-197 show , 1-200, 1-204, 1-215, 1-245, 1-246, 1-248, 1-343, 1-345, 1-361, 1-366, 1-368, 1-417, 1 -450, 1-452, 1-453, 1-456, 1-458, 1-460, 1-463, 1-464, 1-465, 1-468, 1-475, 1-476, 1-488 , 1 -494, 1-517, 1-572, 1-583, 2-2, 2-4, 2-5, 2-6, 2-7, 2-19, 3-2 and 3-16 at one Application rate of 320 g / ha each having at least 90% action against Abutilon theophrasti, Amaranthus retroflexus, Matricara inodora, Stellaria media, Veronica persica and Viola tricolor.
  • test plants Greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or

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Abstract

N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides of the general formula (I) are described as herbicides. In this formula (I), X, Y, Z and R represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. A and B represent N and CY.

Description

N-(Tetrazol-5-yl)- und N-(Triazol-5-yl)arylcarbonsäureamide und ihre Verwendung als Herbizide  N- (tetrazol-5-yl) and N- (triazol-5-yl) arylcarboxamides and their use as herbicides
Beschreibung description
Die Erfindung betrifft das technische Gebiet der Herbizide, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsern in The invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
Nutzpflanzenkulturen. Crops of useful plants.
Aus WO2003/010143 und WO2003/010153 sind N-(Tetrazol-5-yl)- und N-(Triazol-5- yl)benzamide und ihre pharmakologische Wirkung bekannt. Aus der prioritätsälteren, nicht vorveröffentlichen EP101748937 sind bestimmte N-(Tetrazol-5-yl)- und N- (Triazol-5-yl)benzamide und -nicotinamide als Herbizide bekannt. Es wurde nun gefunden, dass (Tetrazol -5-yl)- und N-(Triazol-5-yl)arylcarbonsäureamide und From WO2003 / 010143 and WO2003 / 010153 N- (tetrazol-5-yl) - and N- (triazol-5-yl) benzamides and their pharmacological activity are known. From the earlier priority, not pre-published EP101748937 certain N- (tetrazol-5-yl) - and N- (triazol-5-yl) benzamides and nicotinamides are known as herbicides. It has now been found that (tetrazole-5-yl) - and N- (triazol-5-yl) arylcarbonsäureamide and
-nicotinamide, die in 1 -Position des Tetrazol- bzw. Triazolrings spezielle Substituenten tragen, als Herbizide besonders gut geeignet sind. nicotinamides which carry special substituents in the 1-position of the tetrazole or triazole ring, are particularly suitable as herbicides.
Ein Gegenstand der vorliegenden Erfindung sind somit N-(Tetrazol-5-yl)- und N- (Triazol-5-yl)arylcarbonsäureamide der Formel (I) oder deren Salze An object of the present invention are thus N- (tetrazol-5-yl) - and N- (triazol-5-yl) arylcarbonsäureamide of formula (I) or salts thereof
Figure imgf000003_0001
worin
Figure imgf000003_0001
wherein
A bedeutet N oder CY, B bedeutet N oder CH, X bedeutet Nitro, Halogen, Cyano, Formyl, Rhodano, (Ci-C6)-Alkyl, Halogen-(Ci- C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)- alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)NR1OR1, OR1, OCOR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)- Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)- Alkyl-SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl- NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, NR1R2, P(O)(OR5)2, CH2P(O)(OR5)2, (Ci-C6)- Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die beiden letztgenannten Reste jeweils durch s Reste Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, und wobei Heterocyclyl n Oxogruppen trägt, Y bedeutet Wasserstoff, Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR1, A is N or CY, B is N or CH, X is nitro, halogen, cyano, formyl, thiocyanato, (Ci-C6) alkyl, halo (Ci- C6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl , (C2-C6) alkynyl, halo (C 3 -C 6) - alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O) N (R 1 ) 2 , OC (O) N (R 1 ) 2 , C (O) NR 1 OR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S ( O) n R 2 , SO 2 OR 1 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -alkyl-CO 2 R 1 , ( Ci-C 6) - alkyl-SO 2 OR 1, (Ci-C 6) alkyl-CON (R 1) 2, (Ci-C 6) alkyl-SO 2 N (R 1) 2, (Ci- C 6 ) -Alkyl- NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , NR 1 R 2 , P (O) (OR 5 ) 2 , CH 2 P (O) (OR 5 ) 2 , (C 1 -C 6) -alkyl heteroaryl, (C 1 -C 6) -alkyl heterocyclyl, where the last two radicals are each represented by s radicals halogen, (C 1 -C 6) -alkyl, Halogeno (C 1 -C 6) -alkyl, S (O) n - (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy, halogeno (C 1 -C 6) -alkoxy, and where heterocyclyl carries n oxo groups, Y is hydrogen, nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C2-C6) alkynyl, halo (C 2 - C6) -alkynyl, (C3-C6) -cycloalkyl, (C3-C6) cycloalkenyl, halo (C3-C6) cycloalkyl, (C3-C6 ) -Cycloalkyl- (C 1 -C 6 ) -alkyl, halogen- (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 ,
COOR1,OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O) N (R 1 ) 2 , OC (O) N (R 1 ) 2 ,
CO(NOR1)R1, NR1SO2R2, NR1COR1, OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2 (C1- C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)-Alkyl-CN, (Ci-C6)-Alkyl-SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, N(R1)2, P(O)(OR5)2, CH2P(O)(OR5)2, (Ci-C6)-Alkyl-Phenyl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)- Alkyl-Heterocyclyl, Phenyl, Heteroaryl oder Heterocyclyl, wobei die letzten 6 Reste jeweils durch s Reste aus der Gruppe Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci- C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C4)-alkyl und Cyanonnethyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, CO (NOR 1 ) R 1 , NR 1 SO 2 R 2 , NR 1 COR 1 , OR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2 OR 1 , SO 2 N (R 1 ) 2 (C 1 -C 6 ) -Alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (Ci -C 6) alkyl-CO 2 R 1, (Ci-C 6) -alkyl-CN, (Ci-C 6) -alkyl-SO 2 OR 1, (Ci-C 6) alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , N (R 1 ) 2 , P (O) (OR 5 ) 2 , CH 2 P (O) (OR 5 ) 2 , (C 1 -C 6 ) -alkyl-phenyl, (C 1 -C 6 ) -alkyl heteroaryl, (Ci-C 6) - alkyl-heterocyclyl, phenyl, heteroaryl, or heterocyclyl, where the last 6 residues (respectively by s radicals selected from the group halogen, nitro, cyano, (Ci-C6) alkyl, halo Ci C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (Ci -C 6) alkoxy- (C 1 -C 4 ) -alkyl and cyanoethyl, and wherein heterocyclyl carries n oxo groups,
Z bedeutet Halogen, Cyano, Rhodano, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)- cycloalkyl-(Ci-C6)-alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)NR1OR1, OSO2R2, S(O)nR2, SO2OR1 , SO2N(R1)2, NR1SO2R2, NR1COR1, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)-Alkyl-SO2OR1, (Ci-C6)-Alkyl- CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, N(R1)2, P(O)(OR5)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die letzten drei Reste jeweils durch s Reste aus der Gruppe Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy oder Halogen- (Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder Z kann auch Wasserstoff, (Ci-Ce)-Alkyl oder (Ci-Ce)-Alkoxy bedeuten, falls Y für den Rest S(O)nR2 steht, Z represents halogen, cyano, rhodano, halo (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, halogeno (C 2 -C 6 ) -alkynyl, -C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, halo (C 3 - C 6 ) - cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O) N (R 1 ) 2 , OC (O) N (R 1 ) 2 , C (O) NR 1 OR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2 OR 1 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , ( C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -alkyl-CO 2 R 1 , (C 1 -C 6 ) -alkyl-SO 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , N (R 1 ) 2 , P (O) (OR 5 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals each consist of s radicals of the group halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl , (C 1 -C 6) -alkoxy or halogeno (C 1 -C 6) -alkoxy, and where heterocyclyl carries n oxo groups, or Z may also denote hydrogen, (C 1 -C 6) -alkyl or (C 1 -C 6) -alkoxy if Y is the radical S (O) n R 2 ,
R bedeutet CH2R6, R is CH 2 R 6 ,
durch m Oxogruppen substituiertes CH2-Heterocyclyl, by m oxo groups substituted CH 2 heterocyclyl,
durch t (Ci-C6)-Alkylgruppen substituiertes (C3-C7)-Cycloalkyl, (C 3 -C 7) -cycloalkyl substituted by t (C 1 -C 6) -alkyl groups,
jeweils durch u Reste aus der Gruppe bestehend aus Nitro, Cyano, Hydroxy, Oxo, SiR5 3, PO(OR5)2, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, N(R3)2, COR3, OCOR3, NR3COR3, NR3SO2R4, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl substituiertes (C2-C6)- Alkyl, (C3-C7)-Cycloalkyl, Halogen-(C2-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl oder Halogen-(C2-C6)-alkinyl, wobei die Reste (C3-C6)-in each case by u radicals from the group consisting of nitro, cyano, hydroxyl, oxo, SiR 5 3 , PO (OR 5 ) 2 , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - alkoxy, halo (Ci-C 6) -alkoxy, N (R 3) 2, COR 3, OCOR 3, NR 3 COR 3, NR 3 SO 2 R 4, (C 3 -C 6) -cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl substituted (C 2 -C 6) - alkyl, (C 3 -C 7) cycloalkyl, halo (C 2 -C 6) alkyl , (C 2 -C 6) alkenyl, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl or halo (C 2 -C 6) -alkynyl, where the radicals (C3-C6 ) -
Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl jeweils durch s Substituenten aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Cyano, Nitro, Trifluormethyl und Halogen substituiert sind, und wobei Heterocyclyl und Cycloalkyl n Oxogruppen tragen, Cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each substituted by s substituents selected from the group consisting of methyl, ethyl, methoxy, cyano, nitro, trifluoromethyl and halo, and wherein Heterocyclyl and cycloalkyl carry n oxo groups,
Q bedeutet O, S oder NR3, Q is O, S or NR 3 ,
R1 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR3-Heteroaryl, (Ci-C6)-Alkyl-NR3-Heterocyclyl wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4 CO2R3, COSR4, CON(R3)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R2 bedeutet (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2-C6)-R 1 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 - C 6) haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O - (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) - alkyl heteroaryl, Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) alkyl-O-heteroaryl, (Ci-C 6) - alkyl-O-heterocyclyl, (Ci-C 6) - Alkyl-NR 3 -Heteroaryl, (Ci-C 6 ) -alkyl-NR 3 -Heterocyclyl wherein the 21 latter radicals by s radicals from the group consisting of Cyano, halogen, nitro, thiocyanato, OR 3, S (O) n R 4, N (R 3) 2, NR 3 OR 3, COR 3, OCOR 3, SCOR 4, NR 3 COR 3, NR 3 SO 2 R 4 CO 2 R 3 , COSR 4 , CON (R 3 ) 2 and (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) -alkoxycarbonyl are substituted, and wherein heterocyclyl n carries oxo groups, R 2 is (Ci- C 6) alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -
Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocyclyl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci- C6)-Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR3-Heteroaryl, (Ci-C6)-Alkyl-NR3-Heterocyclyl wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4, CO2R3, COSR4, CON(R3)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 -C 6) - cycloalkenyl, (C3-C 6) halocycloalkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl- (C 1 -C 6 ) -alkyl , Heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O- Heterocyclyl, (C 1 -C 6 ) -alkyl-NR 3 -heteroaryl, (C 1 -C 6 ) -alkyl-NR 3 -heterocyclyl where the last-mentioned radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, rhodano, OR 3 , S (O) n R 4 , N (R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 4 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , COSR 4 , CON (R 3 ) 2 and (C 1 -C 4 ) -alkoxy- (C 2 -C 6 ) -alkoxycarbonyl, and wherein heterocyclyl carries n oxo groups,
R3 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) - Cycloalkyl- (C 1 -C 6 ) -alkyl,
R4 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl oder (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, R 4 is (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkynyl, (C3-C6) -cycloalkyl or (C3-C6) -cycloalkyl- ( C 1 -C 6 ) -alkyl,
R5 bedeutet (Ci-C4)-Alkyl, R 5 is (C 1 -C 4 ) -alkyl,
R6 bedeutet OCOOR4, NR4COOR4, S(O)n-(Ci-C6)-Alkyl, S(O)n-(Ci-C6)-Haloalkyl, Nitro, Cyano, SiR53, PO(OR5)2, Heterocyclyl oder Cycloalkyl, wobei die beiden letztgenannten Reste m Oxo- oder Hydroxygruppen tragen, m bedeutet 1 oder 2, R 6 is OCOOR 4 , NR 4 COOR 4 , S (O) n - (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -haloalkyl, nitro, cyano, SiR 5 3, PO (OR 5 ) 2 , heterocyclyl or cycloalkyl, where the last two radicals m bear oxo or hydroxy groups, m is 1 or 2,
n bedeutet 0, 1 oder 2, n is 0, 1 or 2,
s bedeutet 0, 1 , 2 oder 3, s is 0, 1, 2 or 3,
t bedeutet 1 , 2, 3 oder 4, t is 1, 2, 3 or 4,
u bedeutet 1 , 2, 3, 4 oder 5. In der Formel (I) und allen nachfolgenden Formeln können Alkylreste mit mehr als zwei Kohlenstoffatomen geradkettig oder verzweigt sein. Alkylreste bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1 ,3-Dimethylbutyl. Analog bedeutet Alkenyl z.B. Allyl, 1 -Methyl prop-2-en-1 -yl, u is 1, 2, 3, 4 or 5. In formula (I) and all subsequent formulas, alkyl radicals having more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl. Analogously, alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl,
2-Methyl-prop-2-en-1 -yl, But-2-en-1 -yl, But-3-en-1 -yl, 1 -Methyl-but-3-en-1 -yl und 1 -Methyl-but-2-en-1 -yl. Alkinyl bedeutet z.B. Propargyl, But-2-in-1 -yl, But-3-in-1 -yl, 1 -Methyl-but-3-in-1 -yl. Die Mehrfachbindung kann sich jeweils in beliebiger Position des ungesättigten Rests befinden. Cycloalkyl bedeutet ein carbocyclisches, gesättigtes Ringsystem mit drei bis sechs C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. Analog bedeutet Cycloalkenyl eine monocyclische Alkenylgruppe mit drei bis sechs Kohlenstoffringgliedern, z.B. Cyclopropenyl, Cyclobutenyl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1 - Methyl-but-2-en-1-yl. Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl. The multiple bond can each be in any position of the unsaturated radical. Cycloalkyl means a carbocyclic saturated ring system having three to six C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, e.g. Cyclopropenyl, cyclobutenyl,
Cyclopentenyl und Cyclohexenyl, wobei sich die Doppelbindung an beliebiger Position befinden kann. Halogen steht für Fluor, Chlor, Brom oder lod. Cyclopentenyl and cyclohexenyl, wherein the double bond may be in any position. Halogen is fluorine, chlorine, bromine or iodine.
Heterocyclyl bedeutet einen gesättigten, teilgesättigten oder vollständig ungesättigten cyclischen Rest, der 3 bis 6 Ringatome enthält, von denen 1 bis 4 aus der Gruppe Sauerstoff, Stickstoff und Schwefel stammen, und der zusätzlich durch einen Heterocyclyl means a saturated, partially saturated or fully unsaturated cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group oxygen, nitrogen and sulfur, and additionally by a
Benzoring annelliert sein kann. Beispielsweise steht Heterocyclyl für Piperidinyl, Pyrrolidinyl, Tetrahydrofuranyl, Dihydrofuranyl und Oxetanyl. Heteroaryl bedeutet einen aromatischen cyclischen Rest, der 3 bis 6 Ringatome enthält, von denen 1 bis 4 aus der Gruppe Sauerstoff, Stickstoff und Schwefel stammen, und der zusätzlich durch einen Benzoring annelliert sein kann. Beispielsweise steht Heteroaryl für Benzoring can be annealed. For example, heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl. Heteroaryl means an aromatic cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group consisting of oxygen, nitrogen and sulfur, and may additionally be fused by a benzo ring. For example, heteroaryl stands for
Benzimidazol-2-yl, Furanyl, Imidazolyl, Isoxazolyl, Isothiazolyl, Oxazolyl, Pyrazinyl, Pyrimidinyl, Pyridazinyl, Pyridinyl, Benzisoxazolyl, Thiazolyl, Pyrrolyl, Pyrazolyl, Thiophenyl, 1 ,2,3-Oxadiazolyl, 1 ,2,4-Oxadiazolyl, 1 ,2,5-Oxadiazolyl, 1 ,3,4-Oxadiazolyl, 1 ,2,4-Triazolyl, 1 ,2,3-Triazolyl, 1 ,2,5-Triazolyl, 1 ,3,4-Triazolyl, 1 ,2,4-Triazolyl, 1 ,2,4- Thiadiazolyl, 1 ,3,4-Thiadiazolyl, 1 ,2,3-Thiadiazolyl, 1 ,2,5-Thiadiazolyl, 2H-1 , 2,3,4- Tetrazolyl, 1 H-1 ,2,3,4-Tetrazolyl, 1 ,2,3,4-Oxatriazolyl, 1 ,2,3,5-Oxatriazolyl, 1 ,2,3,4- Thiatriazolyl und 1 ,2,3,5-Thiatriazolyl. Benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1, 2,3-oxadiazolyl, 1, 2,4-oxadiazolyl, 1, 2,5-oxadiazolyl, 1, 3,4-oxadiazolyl, 1, 2,4-triazolyl, 1, 2,3-triazolyl, 1, 2,5-triazolyl, 1, 3,4-triazolyl, 1, 2,4-triazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,3-thiadiazolyl, 1, 2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1 H-1, 2,3,4-tetrazolyl, 1, 2,3,4-oxatriazolyl, 1, 2,3,5-oxatriazolyl, 1, 2,3,4-thiatriazolyl and 1, 2,3,5 -Thiatriazolyl.
Ist eine Gruppe mehrfach durch Reste substituiert, so kann diese Gruppe durch ein oder mehrere gleiche oder verschiedene der genannten Reste substituiert sein. Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und If a group is repeatedly substituted by radicals, this group may be substituted by one or more identical or different radicals. Depending on the nature and linkage of the substituents, the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, then enantiomers and
Diastereomere auftreten. Ebenso treten Stereoisomere auf, wenn n für 1 steht Diastereomers occur. Likewise, stereoisomers occur when n is 1
(Sulfoxide). Stereoisomere lassen sich aus den bei der Herstellung anfallenden (Sulfoxides). Stereoisomers can be obtained from the resulting in the preparation
Gemischen nach üblichen Trennmethoden, beispielsweise durch chromato-graphische Trennverfahren, erhalten. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Mixtures according to customary separation methods, for example by chromatographic separation methods obtained. Likewise, stereoisomers can be prepared by using stereoselective reactions using optically active starting materials and / or
Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft auch alle Stereo-isomeren und deren Gemische, die von der allgemeinen Formel (I) umfasst, jedoch nicht spezifisch definiert sind. Auxiliaries are selectively produced. The invention also relates to all stereoisomers and mixtures thereof, which are of the general formula (I) but are not specifically defined.
Bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Preference is given to compounds of the general formula (I) in which
A bedeutet N oder CY, A is N or CY,
B bedeutet N oder CH, B is N or CH,
X bedeutet Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3- C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR1, OR1, OCOR1, OSO2R2, S(O)nR2, SO2OR1 , SO2N(R1)2, NR1SO2R2, NR1COR1, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)-Alkyl-SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl- NR1COR1 oder (Ci-C6)-Alkyl-NR1SO2R2, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl- Heterocyclyl, wobei die beiden letztgenannten Reste jeweils durch s Reste Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci- C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, X is nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C 2 -C 4 ) -alkenyl -C 6) alkynyl, halo (C3-C6) -alkynyl, (C 3 - C 6) cycloalkyl, halo (C3-C6) cycloalkyl, Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, halo (C3-C6) cycloalkyl- (Ci-C 6) alkyl, COR 1, OR 1 , OCOR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2OR 1 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -Alkyl-CO 2 R 1 , (C 1 -C 6 ) -alkyl-SO 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 or (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 ) -alkyl heteroaryl, (Ci C 6 ) alkyl heterocyclyl, where the last two radicals are each represented by s radicals halogen, (Ci-C 6 ) alkyl, halogeno (Ci-C 6 ) alkyl, S (O) n - (Ci-C 6 ) alkyl, (C 1 -C 6 ) alkoxy, halo (C 1 -C 6) alkoxy, and wherein i carries heterocyclyl n oxo groups,
Y bedeutet Wasserstoff, Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3- C6)-alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR1, OR1, COOR1, OSO2R2, S(O)nR2, SO2OR1, SO2 N(R1)2, N(R1)2, NR1SO2R2, NR1COR1, (C1- C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)-Alkyl-SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl- SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, (Ci-C6)-Alkyl-Phenyl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, Phenyl, Heteroaryl oder Y is hydrogen, nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, or halogen- (C 2 -C 6 ) -alkenyl , (C 2 -C 6 ) -alkynyl, halogeno (C 3 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, halogeno (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl, C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , OR 1 , COOR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2OR 1 , SO 2 N (R 1 ) 2 , N (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C1- C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (Ci-C 6 ) -alkyl-CO 2 R 1 , (Ci-C 6 ) -alkyl-SO 2 OR 1 , (Ci-C 6 ) -alkyl-CON (R 1 ) 2 , (Ci-C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 ) -Alkyl-phenyl, (Ci-C6) -alkyl-heteroaryl, (Ci-C6) -alkyl-heterocyclyl, phenyl, heteroaryl or
Heterocyclyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)- Alkoxy-(Ci-C4)-alkyl und Cyanomethyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Heterocyclyl, where the six last-mentioned radicals each substituted by s radicals selected from the group halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, S (O) n - (Ci-C 6) -alkyl, (Ci-Ce) alkoxy, halo (Ci-C 6) alkoxy, (Ci-C6) - alkoxy- (Ci-C4) - substituted alkyl and cyanomethyl, and wherein heterocyclyl n carries oxo groups,
Z bedeutet Halogen, Cyano, Rhodano, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)- cycloalkyl-(Ci-C6)-alkyl, COR1, COOR1, C(O)N(R1)2, C(O)NR1OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)-Alkyl- SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, 1 ,2,4-Triazol-1 -yl, oder Z represents halogen, cyano, thiocyanato, halo (Ci-C6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halogen - (C 3 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, halogeno (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno- (C 3 -C 6 ) -alkyl C 3 -C 6) - cycloalkyl- (Ci-C 6) alkyl, COR 1, COOR 1, C (O) N (R 1) 2, C (O) NR 1 OR 1, OSO 2 R 2, S (O) n R 2 , SO 2 OR 1 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -alkyl-CO 2 R 1 , (C 1 -C 6 ) -alkyl- SO 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , 1, 2,4-triazol-1-yl, or
Z kann auch Wasserstoff, (Ci-Ce)-Alkyl oder (Ci-Ce)-Alkoxy bedeuten, falls Y für den Rest S(O)nR2 steht, Z can also be hydrogen, (C 1 -C 6) -alkyl or (C 1 -C 6) -alkoxy, if Y is the radical S (O) n R 2 ,
R bedeutet CH2R6, R is CH 2 R 6 ,
durch m Oxogruppen substituiertes CH2-Heterocyclyl, by m oxo groups substituted CH 2 heterocyclyl,
jeweils durch u Reste aus der Gruppe bestehend aus Nitro, Cyano, Hydroxy, Oxo, SiR5 3, PO(OR5)2, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, N(R3)2, COR3, OCOR3, NR3COR3, NR3SO2R4, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl substituiertes (C2-C6)- Alkyl, (C3-C7)-Cycloalkyl, Halogen-(C2-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl oder Halogen-(C2-C6)-alkinyl, wobei die Reste (C3-C6)-in each case by u radicals from the group consisting of nitro, cyano, hydroxyl, oxo, SiR 5 3 , PO (OR 5 ) 2 , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - alkoxy, halo (Ci-C 6) -alkoxy, N (R 3) 2, COR 3, OCOR 3, NR 3 COR 3, NR 3 SO 2 R 4, (C 3 -C 6) -cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl substituted (C 2 -C 6) - alkyl, (C 3 -C 7) cycloalkyl, halo (C 2 -C 6) alkyl , (C 2 -C 6) alkenyl, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl or halo (C 2 -C 6) -alkynyl, where the radicals (C3-C6 ) -
Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl jeweils durch s Substituenten aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Cyano, Nitro, Trifluormethyl und Halogen substituiert sind, und wobei Heterocyclyl und Cycloalkyl n Oxogruppen tragen, Q bedeutet O, S oder NR3, Cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each substituted by s substituents selected from the group consisting of methyl, ethyl, methoxy, cyano, nitro, trifluoromethyl and halo, and wherein Heterocyclyl and cycloalkyl carry n oxo groups, Q is O, S or NR 3 ,
R1 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci-Ce)-Alkyl- Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci-Ce)-Alkyl- NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei die 16 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, NR3COR3, NR3SO2R4, CO2R3, CON(R3)2 und (Ci-C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 1 represents hydrogen, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) - Alkyl-heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl-heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 4) -alkyl- NR 3 heteroaryl or (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, where the last-mentioned radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, OR 3 , S (O) n R 4 , N ( R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , CON (R 3 ) 2 and (C 1 -C 4 ) -alkoxy- C 2 -C 6) alkoxycarbonyl are substituted, and wherein heterocyclyl n carries oxo groups,
R2 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-Ce)- alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (C1 -C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (C1 -C6)-Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, NR3SO2R4, COR3, OCOR3, NR3COR3, CO2R3, CON(R3)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 2 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 4) -alkyl C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 6 ) -Alkyl-NR 3 -heteroaryl or (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, where these radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, OR 3 , S (O) n R 4 , N (R 3 ) 2 , NR 3 OR 3 , NR 3 SO 2 R 4 , COR 3 , OCOR 3 , NR 3 COR 3 , CO 2 R 3 , CON (R 3 ) 2 and (C 1 -C 4 ) alkoxy - (C 2 -C 6 ) alkoxycarbonyl are substituted, and wherein heterocyclyl n carries oxo groups,
R3 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl,
R4 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Al kenyl oder (C2-C6)-Al kinyl, R5 bedeutet Methyl oder Ethyl, R6 bedeutet OCOOR4, NR4COOR4, S(O)n-(Ci-C6)-Alkyl, S(O)n-(Ci-C6)-Haloalkyl, Nitro, Cyano, SiR53, PO(OR5)2 oder Heterocyclyl, das m Oxogruppen trägt, m bedeutet 1 oder 2, R 4 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl or (C 2 -C 6 ) -alkynyl, R 5 is methyl or ethyl, R 6 is OCOOR 4 , NR 4 COOR 4 , S (O) n - (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -haloalkyl, nitro, cyano, SiR 5 3, PO (OR 5 ) 2 or heterocyclyl, the m is oxo, m is 1 or 2,
n bedeutet 0, 1 oder 2, s bedeutet 0, 1 , 2 oder 3, n is 0, 1 or 2, s is 0, 1, 2 or 3,
u bedeutet 1 , 2, 3, 4 oder 5. u is 1, 2, 3, 4 or 5.
Besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), worin Particular preference is given to compounds of the general formula (I) in which
A bedeutet N oder CY, A is N or CY,
B bedeutet N oder CH, X bedeutet Nitro, Halogen, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl, OR1, S(O)nR2, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl- CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die beiden letztgenannten Reste jeweils durch s Reste Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci- C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei B is N or CH, X is nitro, halo, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, OR 1, S (O ) n R 2 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , (Ci -C 6) -alkyl heteroaryl, (C 1 -C 6) -alkyl heterocyclyl, where the latter two radicals are each represented by s radicals halogen, (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkyl, S (O ) n - (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy, halo (C 1 -C 6) alkoxy, and wherein
Heterocyclyl n Oxogruppen trägt, Heterocyclyl carries n oxo groups,
Y Wasserstoff, Nitro, Halogen, Cyano, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, OR1, S(O)nR2, SO2N(R1)2, N(R1)2, NR1SO2R2, NR1COR1, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)- Alkyl-OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, (Ci-C6)-Alkyl-Phenyl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl- Heterocyclyl, Phenyl, Heteroaryl oder Heterocyclyl, wobei die letzten 6 Reste jeweils durch s Reste aus der Gruppe Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-Ce)- alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C4)-alkyl und Cyanomethyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Y is hydrogen, nitro, halogen, cyano, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, OR 1, S (O) n R 2, SO 2 N (R 1) 2, N (R 1) 2, NR 1 SO 2 R 2, NR 1 COR 1, (Ci-C 6) alkyl-S (O) n R 2, (Ci-C 6) - alkyl-OR 1, (Ci-C 6 ) -Alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) - Alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 ) -alkyl-phenyl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) -alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, where the last 6 radicals in each case by s radicals from the group halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - ( C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl and cyanomethyl are substituted, and wherein Heterocyclyl carries n oxo groups,
Z bedeutet Halogen, Cyano, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)nR2, 1 ,2,4-Triazol-1 -yl, oder Z kann auch Wasserstoff, Methyl, Methoxy oder Ethoxy bedeuten, falls Y für den Rest S(O)nR2 steht, Z represents halogen, cyano, halo (Ci-C 6) alkyl, (C3-C6) -cycloalkyl, S (O) n R 2, 1, 2,4-triazol-1-yl, or Z may also be Is hydrogen, methyl, methoxy or ethoxy, if Y is the radical S (O) n R 2 ,
R bedeutet CH2R6, R is CH 2 R 6 ,
CH2-Heterocyclyl, wobei Heterocyclyl m Oxogruppen trägt, jeweils durch u Reste aus der Gruppe bestehend aus Nitro, Cyano, Hydroxy, Oxo, SiR5 3, PO(OR5)2, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, N(R3)2, COR3, OCOR3, NR3COR3, NR3SO2R4, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl substituiertes (C2-C6)- Alkyl, (C3-C7)-Cycloalkyl, Halogen-(C2-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl oder Halogen-(C2-C6)-alkinyl, wobei die Reste (C3-C6)- Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl jeweils durch s Substituenten aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Cyano, Nitro, Trifluormethyl und Halogen substituiert sind, und wobei Heterocyclyl und Cycloalkyl n Oxogruppen tragen, CH 2 heterocyclyl, wherein heterocyclyl m carries oxo groups, in each case by u radicals from the group consisting of nitro, cyano, hydroxyl, oxo, SiR 5 3 , PO (OR 5 ) 2 , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - alkoxy, halo (Ci-C 6) -alkoxy, N (R 3) 2, COR 3, OCOR 3, NR 3 COR 3, NR 3 SO 2 R 4, (C 3 -C 6) -cycloalkyl, heteroaryl, Heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl substituted (C 2 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, halo (C 2 -C 6 ) -alkyl, ( C 2 -C 6 ) alkenyl, halogeno (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl or halo (C 2 -C 6 ) alkynyl, where the radicals (C 3 -C 6 ) -cycloalkyl, heteroaryl , Heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each substituted by s substituents selected from the group consisting of methyl, ethyl, methoxy, cyano, nitro, trifluoromethyl and halo, and wherein heterocyclyl and cycloalkyl n carry oxo groups,
Q bedeutet O, S oder NR3, Q is O, S or NR 3 ,
R1 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, Phenyl,R 1 represents hydrogen, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl,
Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci-Ce)-Alkyl- Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci-Ce)-Alkyl- NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei die 16 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, NR3COR3, NR3SO2R4, CO2R3, CON(R3)2 und (Ci-C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl-heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, ( C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 6 ) -alkyl, -NR 3 -heteroaryl or (C 1 -C 6 ) -alkyl-NR 3 -heterocyclyl, where the last-mentioned radicals are represented by s radicals from the group from cyano, halogen, nitro, OR 3 , S (O) n R 4 , N (R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , CON (R 3 ) 2 and (C 1 -C 4 ) -alkoxy- (C 2 -C 6) -alkoxycarbonyl, and where heterocyclyl carries n oxo groups,
R2 bedeutet (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, wobei diese drei vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen und OR3 substituiert sind, R 2 is (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, where these three radicals mentioned above are each represented by s radicals from the group consisting of Group consisting of halogen and OR 3 are substituted,
R3 bedeutet Wasserstoff oder (Ci-C6)-Alkyl, bedeutet (Ci-C6)-Alkyl, R 3 is hydrogen or (C 1 -C 6 ) -alkyl, is (C 1 -C 6 ) -alkyl,
R5 bedeutet Methyl oder Ethyl, R6 bedeutet OCOOR4, NR4COOR4, S(O)n-(Ci-C6)-Alkyl, S(O)n-(Ci-C6)-Haloalkyl, Nitro, Cyano, SiR5 3, PO(OR5)2, m bedeutet 1 oder 2, R 5 is methyl or ethyl, R 6 is OCOOR 4 , NR 4 COOR 4 , S (O) n- (C 1 -C 6 ) -alkyl, S (O) n- (C 1 -C 6 ) -haloalkyl, nitro, cyano, SiR 5 3 , PO (OR 5 ) 2 , m is 1 or 2,
n bedeutet 0, 1 oder 2, n is 0, 1 or 2,
s bedeutet 0, 1 , 2 oder 3, s is 0, 1, 2 or 3,
u bedeutet 1 , 2, 3, 4 oder 5. u is 1, 2, 3, 4 or 5.
In allen nachfolgend genannten Formeln haben die Substituenten und Symbole, sofern nicht anders definiert, dieselbe Bedeutung wie unter Formel (I) beschrieben. In all of the formulas below, the substituents and symbols, unless otherwise defined, have the same meaning as described for formula (I).
Erfindungsgemäße Verbindungen können beispielsweise nach der in Schema 1 angegebenen Methode durch basen katalysierte Umsetzung eines Benzoesäure- Chlorids (II) mit einem 5-Amino-1 -H-1 ,2,4-triazol, bzw. 5-Amino-1 H-tetrazol (III) hergestellt werden: Compounds of the invention can be prepared, for example, by the method indicated in Scheme 1, by base catalyzed reaction of a benzoic acid chloride (II) with a 5-amino-1 -H-1, 2,4-triazole, or 5-amino-1H-tetrazole (III) are prepared:
Schema 1 Scheme 1
Figure imgf000013_0001
Figure imgf000013_0001
(III) (II) (I)  (III) (II) (I)
Die Benzoesäurechloride der Formel (II) beziehungsweise die ihnen zugrunde liegenden Benzoesäuren sind grundsätzlich bekannt und können beispielsweise gemäß den in US 6,376,429 B1 , EP 1 585 742 A1 und EP 1 202 978 A1  The benzoic acid chlorides of the formula (II) or the benzoic acids on which they are based are known in principle and can be synthesized, for example, according to the processes described in US Pat. No. 6,376,429 B1, EP 1 585 742 A1 and EP 1 202 978 A1
beschriebenen Methoden hergestellt werden. be prepared methods described.
Erfindungsgemäße Verbindungen können auch nach der in Schema 2 angegebenen Methode durch Umsetzung einer Benzoesäure der Formel (IV) mit einem 5-Amino-1 - H-1 ,2,4-triazol, bzw. 5-Amino-1 H-tetrazol (III) hergestellt werden: Schema 2 Compounds according to the invention can also be prepared by the method given in Scheme 2 by reacting a benzoic acid of the formula (IV) with a 5-amino-1-H-1, 2,4-triazole or 5-amino-1H-tetrazole (III ) getting produced: Scheme 2
Figure imgf000014_0001
Figure imgf000014_0001
(III) (IV) (I)  (III) (IV) (I)
Für die Aktivierung können wasserentziehende Reagenzien, die üblicherweise für Amidierungsreaktionen, wie z. B. 1 ,Γ-Carbonyldiimidazol (CDI), Dicyclohexyl- carbodiimid (DCC), 2,4,6-Tripropyl-1 ,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc. eingesetzt werden. For the activation, dehydrating reagents commonly used for amidation reactions, such. B. 1, Γ-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-tripropyl-1, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P) etc . are used.
Erfindungsgemäße Verbindungen können auch nach der in Schema 3 angegebenen Methode durch Umsetzung eines N-(1 H-1 ,2,4-triazol-5-yl)benzamides, N-(1 H-tetrazol- 5-yl)benzamides, N-(1 H-1 ,2,4-triazol-5-yl)nicotinamide oder N-(1 H-tetrazol-5- yl)nicotinamide hergestellt werden: Compounds of the invention can also be prepared by the method given in Scheme 3 by reacting an N- (1H-1, 2,4-triazol-5-yl) benzamide, N- (1H-tetrazol-5-yl) benzamide, N- (1 H-1, 2,4-triazol-5-yl) nicotinamide or N- (1 H -tetrazol-5-yl) nicotinamide are prepared:
Schema 3 Scheme 3
Figure imgf000014_0002
Figure imgf000014_0002
Für diese in Schema 3 genannte Reaktion können Alkylierungsmittel wie Alkyl- halogenide, -sulfonate oder Dialkylsulfate in Gegenwart einer Base eingesetzt werden. Es kann zweckmäßig sein, Reaktionsschritte in ihrer Reihenfolge zu ändern. So sind Benzoesäuren, die ein Sulfoxid tragen, nicht ohne weiteres in ihre Säurechloride zu überführen. Hier bietet sich an, zunächst auf Thioether-Stufe das Amid zu herzustellen und danach den Thioether zum Sulfoxid zu oxidieren. Die 5-Amino-1 H-tetrazole der Formel (III) können analog zu literaturbekannten For this reaction mentioned in Scheme 3, alkylating agents such as alkyl halides, sulfonates or dialkyl sulfates can be used in the presence of a base. It may be convenient to change reaction steps in order. Thus, benzoic acids carrying a sulfoxide are not readily converted into their acid chlorides. Here it is advisable to first produce the amide on the thioether stage and then to oxidize the thioether to the sulfoxide. The 5-amino-1H-tetrazoles of the formula (III) can be prepared analogously to those known from the literature
Methoden hergestellt werden. Beispielsweise können 5-Amino-1 -R-tetrazole nach der in Journal of the American Chemical Society (1954), 76, 923-924 beschriebenen Methode aus Amino-tetrazol hergestellt werden: Methods are produced. For example, 5-amino-1-R-tetrazoles may be added after in Amino-tetrazole method described in Journal of the American Chemical Society (1954), 76, 923-924:
Figure imgf000015_0001
Figure imgf000015_0001
In der oben genannten Formel steht R beispielsweise für einen Alkylrest. 5-Amino-1 -R-tetrazole können zum Beispiel wie in Journal of the American Chemical Society (1954) 76, 88-89 beschrieben, synthetisiert werden: In the abovementioned formula, R is, for example, an alkyl radical. For example, 5-amino-1-R-tetrazoles can be synthesized as described in Journal of the American Chemical Society (1954) 76, 88-89:
R NH R NH
NaN02/HCI N _ ^ NaN0 2 / HCI N _ ^
H H
H NHN
H H
Die 5-Amino-1 H-triazole der Formel (III) können analog zu literaturbekannten The 5-amino-1H-triazoles of the formula (III) can be prepared analogously to those known from the literature
Methoden hergestellt werden. Beispielsweise können 5-Amino-1 -R-triazole nach der Zeitschrift für Chemie (1990), 30(12), 436 - 437 beschriebenen Methode aus Methods are produced. For example, 5-amino-1-R-triazoles according to the Journal of Chemistry (1990), 30 (12), 436-437 described method
Aminotriazol hergestellt werden: Aminotriazole be prepared:
Figure imgf000015_0002
Figure imgf000015_0002
5-Amino-1 -R-triazole können auch zum Beispiel wie in Chemische Berichte (1964), 97(2), 396-404 beschrieben, synthetisiert werden: 5-Amino-1-R-triazoles can also be synthesized, for example, as described in Chemische Berichte (1964), 97 (2), 396-404:
Figure imgf000015_0003
Figure imgf000015_0003
5-Amino-1 -R-triazole können auch zum Beispiel wie in Angewandte Chemie 5-amino-1-R-triazoles can also be used, for example, as in Angewandte Chemie
(1963), 75, 918 beschrieben, synthetisiert werden:
Figure imgf000016_0001
Kollektionen aus Verbindungen der Formel (I) und/oder deren Salzen, die nach den oben genannten Reaktionen synthetisiert werden können, können auch in (1963), 75, 918, are synthesized:
Figure imgf000016_0001
Collections of compounds of the formula (I) and / or their salts, which can be synthesized after the abovementioned reactions, can also be found in
parallelisierter Weise hergestellt werden, wobei dies in manueller, teilweise be prepared in a parallelized manner, this manual, in part
automatisierter oder vollständig automatisierter Weise geschehen kann. Dabei ist es beispielsweise möglich, die Reaktionsdurchführung, die Aufarbeitung oder die automated or completely automated way. It is possible, for example, the reaction procedure, the work-up or the
Reinigung der Produkte bzw. Zwischenstufen zu automatisieren. Insgesamt wird hierunter eine Vorgehensweise verstanden, wie sie beispielsweise durch D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley 1999, auf den Seiten 1 bis 34 beschrieben ist. Zur parallelisierten Reaktionsdurchführung und Aufarbeitung können eine Reihe von im Handel erhältlichen Geräten verwendet werden, beispielsweise Calpyso- Reaktionsblöcke (Caylpso reaction blocks) der Firma Barnstead International, Automate cleaning of products or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34. For the parallelized reaction procedure and workup, a number of commercially available devices can be used, for example Calypyso reaction blocks (Caylpso reaction blocks) from Barnstead International,
Dubuque, Iowa 52004-0797, USA oder Reaktionsstationen (reaction stations) der Firma Radleys, Shirehill, Saffron Waiden, Essex, CB 1 1 3AZ, England oder Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Waiden, Essex, CB 1 1 3AZ, England or
MultiPROBE Automated Workstations der Firma Perkin Elmar, Waltham, MultiPROBE Automated Workstations from Perkin Elmar, Waltham,
Massachusetts 02451 , USA. Für die parallelisierte Aufreinigung von Verbindungen der allgemeinen Formel (I) und deren Salzen beziehungsweise von bei der Herstellung anfallenden Zwischenprodukten stehen unter anderem Chromatographieapparaturen zur Verfügung, beispielsweise der Firma ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.  Massachusetts 02451, United States. For the parallelized purification of compounds of the general formula (I) and their salts or of intermediates obtained during the preparation, among others, chromatography apparatuses are available, for example the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
Die aufgeführten Apparaturen führen zu einer modularen Vorgehensweise, bei der die einzelnen Arbeitsschritte automatisiert sind, zwischen den Arbeitsschritten jedoch manuelle Operationen durchgeführt werden müssen. Dies kann durch den Einsatz von teilweise oder vollständig integrierten Automationssystemen umgangen werden, bei denen die jeweiligen Automationsmodule beispielsweise durch Roboter bedient werden. Derartige Automationssysteme können zum Beispiel von der Firma Caliper, Hopkinton, MA 01748, USA bezogen werden. Die Durchführung einzelner oder mehrerer Syntheseschritte kann durch den Einsatz von Polymer-supported reagents/Scavanger-Harze unterstützt werden. In der The listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed. This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA. The implementation of single or multiple synthetic steps can be supported by the use of polymer-supported reagents / Scavanger resins. In the
Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in ChemFiles, Vol. 4, No. 1 , Polymer-Supported Scavengers and Reagents for Solution- Phase Synthesis (Sigma-Aldrich). Technical literature describes a number of experimental protocols, for example in ChemFiles, Vol. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).
Neben den hier beschriebenen Methoden kann die Herstellung von Verbindungen der allgemeinen Formel (I) und deren Salzen vollständig oder partiell durch Festphasen unterstützte Methoden erfolgen. Zu diesem Zweck werden einzelne Zwischenstufen oder alle Zwischenstufen der Synthese oder einer für die entsprechende In addition to the methods described herein, the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis or one for the corresponding
Vorgehensweise angepassten Synthese an ein Syntheseharz gebunden. Festphasen- unterstützte Synthesemethoden sind in der Fachliteratur hinreichend beschrieben, z.B. Barry A. Bunin in "The Combinatorial Index", Verlag Academic Press, 1998 und  Approach adapted synthesis bound to a synthetic resin. Solid phase assisted synthetic methods are well described in the literature, e.g. Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998 and
Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley, 1999. Die Verwendung von Festphasen- unterstützten Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999. The use of solid phase assisted
Synthesemethoden erlaubt eine Reihe von literaturbekannten Protokollen, die wiederum manuell oder automatisiert ausgeführt werden können. Die Reaktionen können beispielsweise mittels IRORI-Technologie in Mikroreaktoren (microreactors) der Firma Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA durchgeführt werden. Synthesis methods allow a number of protocols known from the literature, which in turn can be carried out manually or automatically. The reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
Sowohl an fester als auch in flüssiger Phase kann die Durchführung einzelner oder mehrerer Syntheseschritte durch den Einsatz der Mikrowellen-Technologie unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in Microwaves in Organic and Medicinal Chemistry (Herausgeber C. O. Kappe und a. Stadler), Verlag Wiley, 2005. Both solid and liquid phases can be supported by the implementation of single or multiple synthetic steps through the use of microwave technology. A number of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (publishers C. O. Kappe and A. Stadler), Verlag Wiley, 2005.
Die Herstellung gemäß der hier beschriebenen Verfahren liefert Verbindungen der Formel (I) und deren Salze in Form von Substanzkollektionen, die Bibliotheken genannt werden. Gegenstand der vorliegenden Erfindung sind auch Bibliotheken, die mindestens zwei Verbindungen der Formel (I) und deren Salzen enthalten. The preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries. The present invention also provides libraries containing at least two compounds of formula (I) and their salts.
Die erfindungsgemäßen Verbindungen der Formel (I) (und/oder deren Salze), im folgenden zusammen als„erfindungsgemäße Verbindungen" bezeichnet, weisen eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wichtiger mono- und dikotyler annueller Schadpflanzen auf. Auch schwer bekämpfbare perennierende Schadpflanzen, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfaßt. The compounds of the formula (I) (and / or salts thereof) according to the invention, hereinafter referred to collectively as "compounds of the invention", have a excellent herbicidal activity against a broad spectrum of important mono- and dicotyledonous weed plants. Also difficult to control perennial harmful plants that expel from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
Gegenstand der vorliegenden Erfindung ist daher auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen oder zur Wachstumsregulierung von Pflanzen, vorzugsweise in Pflanzenkulturen, worin eine oder mehrere erfindungsgemäße The present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, wherein one or more of the present invention
Verbindung(en) auf die Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Compound (s) on the plants (e.g., weeds such as mono- or dicotyledons
Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut (z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen) oder die Fläche, auf der die Pflanzen wachsen (z.B. die Anbaufläche), ausgebracht werden. Dabei können die erfindungsgemäßen Verbindungen z.B. im Vorsaat- (ggf. auch durch Einarbeitung in den Boden), Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyl- octenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Weeds or unwanted crops), the seeds (e.g., grains, seeds or vegetative propagules such as tubers or sprouts with buds) or the area on which the plants grow (e.g., the acreage). The compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufverfahren be applied. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species. Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyl octenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera , Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Dikotyle Unkräuter der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Werden die erfindungsgemäßen Verbindungen vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. If the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die after three to four weeks
vollkommen ab. completely off.
Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. When the active ingredients are applied to the green parts of the plants postemergence, growth stops after the treatment and the harmful plants remain in the growth stage existing at the time of application or die completely after a certain time, so that a weed competition harmful to the crop plants takes place very early and sustainably eliminated.
Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizide Although the compounds of the invention are excellent herbicides
Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Have activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, e.g. dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium,
Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus, Avena,
Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, insbesondere Zea und Triticum, abhängig von der Struktur der jeweiligen Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum, depending on the structure of each
erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Compound of the invention and its application rate only insignificantly damaged or not at all. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in
Pflanzenkulturen wie landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. Crops such as agricultural crops or ornamental plantings.
Darüberhinaus weisen die erfindungsgemäßen Verbindungen (abhängig von ihrer Struktur und der Aufwandmenge) hervorragende wachstumsregulatorische In addition, the compounds of the invention (depending on their structure and the application rate) have excellent growth-regulatory
Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann. Properties on crops. They regulate the plant's metabolism and can thus be used to specifically influence plant ingredients and facilitate harvesting, eg by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. An inhibition of vegetative growth plays in many monocotyledonous and dicotyledonous crops, since, for example, the storage formation can be reduced or completely prevented.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special
Eigenschaften betreffen z. B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt. Properties concern z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfindungsgemäßen Verbindungen in wirtschaftlich bedeutenden transgenen Kulturen von Nutz- und Zierpflanzen, z. B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Vorzugsweise können die erfindungsgemäßen Verbindungen als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. Preferred with respect to transgenic crops is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice and corn or even crops of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables. Preferably, the compounds according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or
gentechnisch resistent gemacht worden sind. have been made genetically resistant.
Bevorzugt ist die Anwendung der erfindungsgemäßen Verbindungen oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz-und Zierpflanzen, z. B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Vorzugsweise können die erfindungsgemäßen Verbindungen als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen Preferably, the application of the compounds of the invention or their salts in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables. The compounds according to the invention can preferably be employed as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant. Conventional ways of producing new plants that have modified properties compared to previously occurring plants exist
beispielsweise in klassischen Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe for example, in classical breeding methods and the generation of mutants. Alternatively, new plants with altered properties can help
gentechnischer Verfahren erzeugt werden (siehe z. B. EP-A-0221044, EP-A-0131624). Beschrieben wurden beispielsweise in mehreren Fällen genetic engineering methods are produced (see eg EP-A-0221044, EP-A-0131624). For example, several cases have been described
gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/1 1376, WO 92/14827, WO 91/19806),  genetic engineering of crops for modification of the starch synthesized in the plants (eg WO 92/1 1376, WO 92/14827, WO 91/19806),
- transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ transgenic crops which are resistant to certain herbicides of the
Glufosinate (vgl. z. B. EP-A-0242236, EP-A-242246) oder Glyphosate  Glufosinate (see, for example, EP-A-0242236, EP-A-242246) or glyphosate
(WO 92/00377) oder der Sulfonylharnstoffe (EP-A-0257993, US-A-5013659) resistent sind,  (WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659) are resistant,
transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit  transgenic crops, for example cotton, with the ability
Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche die  Bacillus thuringiensis toxins (Bt toxins) to produce, which the
Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924, EP-A-0193259).  Make plants resistant to certain pests (EP-A-0142924, EP-A-0193259).
transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/13972).  Transgenic crop plants with modified fatty acid composition (WO 91/13972).
- gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder - genetically modified crops with new content or
Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhte  Secondary materials z. B. new phytoalexins, which increased one
Krankheitsresistenz verursachen (EPA 309862, EPA0464461 )  Disease resistance cause (EPA 309862, EPA0464461)
gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen (EPA 0305398).  genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EPA 0305398).
- Transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige - Transgenic crops that are pharmaceutically or diagnostically important
Proteine produzieren („molecular pharming")  Produce proteins ("molecular pharming")
transgene Kulturpflanzen, die sich durch höhere Erträge oder bessere Qualität auszeichnen  Transgenic crops that are characterized by higher yields or better quality
transgene Kulturpflanzen die sich durch eine Kombinationen z. B. der o. g.  transgenic crops characterized by a combination z. B. the o. G.
neuen Eigenschaften auszeichnen („gene stacking")  characterize new properties ("gene stacking")
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind im Prinzip bekannt, siehe z. B. I. Potrykus und G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, oder Christou, "Trends in Plant Science" 1 (1996) 423-431 ). Numerous molecular biological techniques that can be used to produce novel transgenic plants with altered properties are known in principle. BI Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431).
Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in For such genetic manipulations, nucleic acid molecules can be used in
Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA- Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden, siehe z. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd edition, 1996
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer The production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one
entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines corresponding antisense RNA, a sense RNA to obtain a
Cosuppressionseffekt.es oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA-Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA-Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. Cosuppressionseffekt.es or the expression of at least one appropriately engineered ribozyme that specifically cleaves transcripts of the above gene product. For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad. Sei. USA 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991 ), 95-106). Die Expression der Nukleinsäuremoleküle kann auch in den In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known in the art (see, for example, Braun et al., EMBO J. 1 1 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106). Expression of the nucleic acid molecules can also be found in the
Organellen der Pflanzenzellen stattfinden. Organelles of the plant cells take place.
Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen Pflanzenspezies handeln, d.h., sowohl monokotyle als auch dikotyle Pflanzen. The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Thus, transgenic plants are available, the altered properties by
Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.
Vorzugsweise können die erfindungsgemäßen Verbindungen in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z. B. Dicamba oder gegen Preferably, the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against
Herbizide, die essentielle Pflanzenenzyme, z. B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydroxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind.  Herbicides containing essential plant enzymes, e.g. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydroxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
Bei der Anwendung der erfindungsgemäßen Wirkstoffe in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber In the application of the active compounds according to the invention in transgenic cultures, in addition to the effects to be observed in other cultures
Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Harmful plants often have effects that are specific for application in the particular transgenic culture, such as altered or specially extended weed spectrum that can be controlled
Aufwand mengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. Expense amounts that can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of transgenic crops.
Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen als Herbizide zur Bekämpfung von Schadpflanzen in transgenen Kulturpflanzen. Die erfindungsgemäßen Verbindungen können in Form von Spritzpulvern, emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, welche die erfindungsgemäßen Verbindungen enthalten. The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants. The compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations. The invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
Die erfindungsgemäßen Verbindungen können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, The compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates,
emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and
Wasser-in-ÖI-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), Water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG),
ULV-Formulierungen, Mikrokapseln und Wachse. ULV formulations, microcapsules and waxes.
Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden These individual formulation types are known and will be known in principle
beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", for example, described in: Winnacker-Kuchler, "Chemical Technology",
Band 7, C. Hanser Verlag München, 4. Aufl. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London. Volume 7, C. Hanser Verlag Munich, 4th ed. 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973, K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise The necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are, for example
beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid described in Watkins, Handbook of Insecticides Dust Diluents and Carriers, 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid
Chemistry", 2nd Ed., J. Wiley & Sons, N.Y., C. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J., Sisley and Wood, "Encyclopedia of Chemistry, 2nd Ed., J. Wiley & Sons, NY, C. Marsden, "Solvents Guide", 2nd Ed., Interscience, NY 1963, McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ, Sisley and Wood, "Encyclopedia of
Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt,  Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964, Schonfeldt,
"Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen Pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. Geeignete Safener sind "Surface-active ethylene oxide adducts", Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986. On the basis of these formulations, it is also possible to prepare combinations with other pesticide-active substances, such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and / or growth regulators, for example in the form of a ready-to-use formulation or as a tank mix. Suitable safeners are
beispielsweise Mefenpyr-diethyl, Cyprosulfamid, Isoxadifen-ethyl, Cloquintocet-mexyl und Dichlormid. for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichloromide.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agent, dispersing agent) in addition to the active ingredient, apart from a diluent or inert substance. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines,
Fettalkoholpolyglykolethersulfate, Alkansulfonate, Alkylbenzolsulfonate, Fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates,
ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe lignosulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene-sulfonic acid sodium or oleoylmethyltaurine acid. To prepare the wettable powders are the herbicidal active ingredients
beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den for example, finely ground in conventional equipment such as hammer mills, blower mills and air jet mills and at the same time or subsequently with the
Formulierungshilfsmitteln vermischt. Formulation aids mixed.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem Emulsifiable concentrates are made by dissolving the active ingredient in one
organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie organic solvents e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers). Examples of emulsifiers which may be used are: alkylarylsulfonic acid calcium salts, such as
Ca-Dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as
Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers,
Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Polyoxethylensorbitanester wie z.B. Propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g.
Polyoxyethylensorbitanfettsäureester. Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Polyoxyethylene. Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates may be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally added surfactants, such as the above with the other
Formulierungstypen bereits aufgeführt sind, hergestellt werden. Emulsionen, z.B. ÖI-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen. Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Formulation types already listed are produced. Emulsions, e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types. Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und Extrusion ohne festes Inertmaterial hergestellt. Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. For the preparation of plate, fluid bed, extruder and spray granules, see e.g.
Verfahren in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff, "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57. Method in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq., "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961 , Seiten 81 -96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101 -103. See, for example, GC Klingman, "Weed Control as a Science," John Wiley and Sons, Inc., New York, 1961, pp. 81-96, and JD Freyer, SA Evans, "Weed Control Handbook," for further details on pesticide formulation. 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
Die agrochemischen Zubereitungen enthalten in der Regel 0.1 bis 99 Gew.-%, insbesondere 0.1 bis 95 Gew.-%, erfindungsgemäße Verbindungen. The agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei In wettable powders, the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients. at
emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, emulsifiable concentrates, the active substance concentration can be about 1 to 90,
vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0.05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche preferably 5 to 80 wt .-% amount. Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which
Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser Granulation aids, fillers, etc. are used. In the water
dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. dispersible granules, the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, In addition, the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving,
Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Antifreeze and solvents, fillers, carriers and dyes, defoamers,
Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel. Evaporation inhibitors and pH and viscosity affecting agents.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen Pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix. On the basis of these formulations, combinations with other pesticidally active substances, such as e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix.
Als Kombinationspartner für die erfindungsgemäßen Verbindungen in As a combination partner for the compounds of the invention in
Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA- Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Mixture formulations or in the tank mix are, for example, known active substances which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase,
Glutamin-Synthetase, p-Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II, Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441 -445 oder "The Pesticide Manual", 15th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2009 und dort zitierter Literatur beschrieben sind. Als bekannte Herbizide oder Glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 15th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2009 and There cited literature are described. As known herbicides or
Pflanzenwachstumsregulatoren, die mit den erfindungsgemäßen Verbindungen kombiniert werden können, sind z.B. folgende Wirkstoffe zu nennen (die Verbindungen sind entweder mit dem "common name" nach der International Organization for Standardization (ISO) oder mit dem chemischen Namen oder mit der Codenummer bezeichnet) und umfassen stets sämtliche Anwendungsformen wie Säuren, Salze, Ester und Isomere wie Stereoisomere und optische Isomere. Dabei sind beispielhaft eine und zum Teil auch mehrere Anwendungsformen genannt: Acetochlor, Acibenzolar, Acibenzolar-S-methyl, Acifluorfen, Acifluorfen-sodium,Plant growth regulators which can be combined with the compounds of the invention are e.g. the following active ingredients (the compounds are denoted either by the "common name" according to the International Organization for Standardization (ISO) or the chemical name or with the code number) and always include all forms of use such as acids, salts, esters and isomers such as stereoisomers and optical isomers. One and in part also several application forms are mentioned by way of example: acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium,
Adonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodiunn, Ametryn, Amicarbazone, Amidochlor, Amidosulfuron, Aminocyclopyrachlor, Aminopyralid, Amitrole, Adonifen, alachlor, allidochlor, alloxydim, alloxydim-sodiunn, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, amitrole,
Ammoniumsulfamat, Ancymidol, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Aziprotryn, Beflubutamid, Benazolin, Benazolin-ethyl, Bencarbazone, Benfluralin, Benfuresate, Bensulide, Bensulfuron, Bensulfuron-methyl, Bentazone, Benzfendizone, Benzobicyclon, Benzofenap, Benzofluor, Benzoylprop, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-natrium, Bispyribac, Bispyribac-natrium, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Bromuron, Buminafos, Busoxinone, Butachlor, Ammonium Sulfamate, Ancymidol, Anilofos, Asulam, Atrazine, Azafenidine, Azimsulfuron, Aziprotryn, Beflubutamide, Benazoline, Benazolin-ethyl, Bencarbazone, Benfluralin, Benfuresate, Bensulide, Bensulfuron, Bensulfuron-methyl, Bentazone, Benzofendizone, Benzobicyclone, Benzofenap, Benzofluor, Benzoylprop, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos Sodium, Bispyribac, Bispyribac Sodium, Bromacil, Bromobutide, Bromofenoxime, Bromoxynil, Bromuron, Buminafos, Busoxinone, Butachlor,
Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylate, Cafenstrole, Carbetamide, Carfentrazone, Carfentrazone-ethyl, Chlomethoxyfen, Chloramben, Chlorazifop, Chlorazifop-butyl, Chlorbromuron, Chlorbufam, Chlorfenac, Chlorfenac- natrium, Chlorfenprop, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlormequat-chlorid, Chlornitrofen, Chlorophthalim, Chlorthal- dimethyl, Chlorotoluron, Chlorsulfuron, Cinidon, Cinidon-ethyl, Cinmethylin, Butafenacil, butamifos, butenachlor, butraline, butroxydim, butylates, cafenstroles, carbetamides, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chloroazifop, chlorazifop-butyl, chlorobromuron, chlorobufam, chlorfenac, chlorfenacsodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, Chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat chloride, chloronitrofen, chlorophthalim, chlorothal-dimethyl, chlorotoluron, chlorosulfuron, cinidone, cinidon-ethyl, cinmethylin,
Cinosulfuron, Clethodim, Clodinafop, Clodinafop-propargyl, Clofencet, Clomazone, Clomeprop, Cloprop, Clopyralid, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cyclanilide, Cycloate, Cyclosulfamuron, Cycloxydim, Cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamides, cyanazines, cyclanilides, cycloates, cyclosulfamuron, cycloxydim,
Cycluron, Cyhalofop, Cyhalofop-butyl, Cyperquat, Cyprazine, Cyprazole, 2,4-D, 2,4- DB, Daimuron/Dymron, Dalapon, Daminozide, Dazomet, n-Decanol, Desmedipham, Desmetryn, Detosyl-Pyrazolate (DTP), Diallate, Dicamba, Dichlobenil, Dichlorprop, Dichlorprop-P, Diclofop, Diclofop-methyl, Diclofop-P-methyl, Diclosulam, Diethatyl, Diethatyl-ethyl, Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Diflufenzopyr- natrium, Dimefuron, Dikegulac-sodium, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimethipin, Dimetrasulfuron, Dinitramine, Dinoseb, Dinoterb, Diphenamid, Dipropetryn, Diquat, Diquat-dibromide, Dithiopyr, Diuron, DNOC, Eglinazine-ethyl, Endothal, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-methyl, Ethephon, Ethidimuron, Ethiozin, Cycluron, Cyhalofop, Cyhalofop-butyl, Cyperquat, Cyprazine, Cyprazole, 2,4-D, 2,4-DB, Daimurone / Dymron, Dalapon, Daminozide, Dazomet, n-Decanol, Desmedipham, Desmetryn, Detosyl-Pyrazolate (DTP) , Dialkylates, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl, diethyl-ethyl, difenoxuron, difenzoquat, diflufenican, difluufenzopyr, difluoropentyrimidate, dimefuron, dikegulac-sodium , Dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipine, dimetrasulfuron, Dinitramine, Dinoseb, Dinoterb, Diphenamid, Dipropetryn, Diquat, Diquat-dibromide, Dithiopyr, Diuron, DNOC, Eglinazine-ethyl, Endothal, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-methyl, Ethephon, Ethidimuron, Ethiozine,
Ethofumesate, Ethoxyfen, Ethoxyfen-ethyl, Ethoxysulfuron, Etobenzanid, F-5331 , d.h. N-[2-Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-1 H-tetrazol-1 -yl]-phenyl]- ethansulfonamid, F-7967, d. h. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-1 H-benzimidazol-4- yl]-1 -methyl-6-(trifluornnethyl)pynnnidin-2,4(1 H,3H)-dion, Fenoprop, Fenoxaprop, Fenoxaprop-P, Fenoxaprop-ethyl, Fenoxaprop-P-ethyl, Fenoxasulfone, Fentrazamide, Fenuron, Flamprop, Flamprop-M-isopropyl, Flamprop-M-methyl, Flazasulfuron, Florasulam, Fluazifop, Fluazifop-P, Fluazifop-butyl, Fluazifop-P-butyl, Fluazolate, Flucarbazone, Flucarbazone-sodium, Flucetosulfuron, Fluchloralin, Flufenacet Ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, F-5331, i. N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide, F-7967 , d. H. 3- [7-chloro-5-fluoro-2- (trifluoromethyl) -1H-benzimidazol-4-yl] -1-methyl-6- (trifluoromethyl) pynnnidine-2,4 (1H, 3H) -dione, Fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop butyl, fluazifop-p-butyl, fluazolates, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet
(Thiafluamide), Flufenpyr, Flufenpyr-ethyl, Flumetralin, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Flumipropyn, Fluometuron, Fluorodifen, (Thiafluamide), Flufenpyr, Flufenpyr-ethyl, Flumetralin, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Flumipropyn, Fluometuron, Fluorodifen,
Fluoroglycofen, Fluoroglycofen-ethyl, Flupoxam, Flupropacil, Flupropanate, Fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate,
Flupyrsulfuron, Flupyrsulfuron-methyl-sodium, Flurenol, Flurenol-butyl, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-meptyl, Flurprimidol, Flurtamone, Fluthiacet, Fluthiacet-methyl, Fluthiamide, Fomesafen, Foramsulfuron, Förch lorfenuron, Flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, förch lorfenuron,
Fosamine, Furyloxyfen, Gibberellinsäure, Glufosinate, Glufosinate-ammonium, Glufosinate-P, Glufosinate-P-ammonium, Glufosinate-P-natrium, Glyphosate, Fosamines, furyloxyfen, gibberellic acid, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate,
Glyphosate-isopropylammonium, H-9201 , d. h. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl- isopropylphosphoramidothioat, Halosafen, Halosulfuron, Halosulfuron-methyl, Glyphosate isopropylammonium, H-9201, d. H. O- (2,4-dimethyl-6-nitrophenyl) -O-ethyl-isopropylphosphoramidothioate, halosafen, halosulfuron, halosulfuron-methyl,
Haloxyfop, Haloxyfop-P, Haloxyfop-ethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop- methyl, Haloxyfop-P-methyl, Hexazinone, HW-02, d. h. l -(Dimethoxyphosphoryl)- ethyl(2,4-dichlorphenoxy)acetat, Imazamethabenz, Imazamethabenz-nnethyl, Haloxyfop, Haloxyfop-P, Haloxyfopethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop- methyl, Haloxyfop-P-methyl, Hexazinone, HW-02, d. H. 1- (dimethoxyphosphoryl) ethyl (2,4-dichlorophenoxy) acetate, imazamethabenz, imazamethabenz-n-ethyl,
Imazamox, Imazamox-ammoniunn, Imazapic, Imazapyr, Imazapyr- isopropylammoniunn, Imazaquin, Imazaquin-amnnoniunn, Imazethapyr, Imazethapyr- ammoniunn, Imazosulfuron, Inabenfide, Indanofan, Indaziflam, Indolessigsäure (IAA), 4-lndol-3-ylbuttersäure (IBA), lodosulfuron, lodosulfuron-methyl-natrium, loxynil, Ipfencarbazone, Isocarbamid, Isopropalin, Isoproturon, Isouron, Isoxaben, Imazamox, imazamoxammonium, imazapic, imazapyr, imazapyrisopropylammonium, imazaquin, imazaquin-amnunnonium, imazethapyr, imazethapyrammonium, imazosulfuron, inabenfide, indanofan, indaziflam, indoleacetic acid (IAA), 4-indol-3-yl-butyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, loxynil, isoparbazone, isocarbamide, isopropalin, isoproturon, isourone, isoxaben,
Isoxachlortole, Isoxaflutole, Isoxapyrifop, KUH-043, d. h. 3-({[5-(Difluormethyl)-1 - methyl-3-(thfluornnethyl)-1 H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dinnethyl-4,5-dihydro-1 ,2- oxazol, Karbutilate, Ketospiradox, Lactofen, Lenacil, Linuron, Maleinsäurehydrazid, MCPA, MCPB, MCPB-methyl, -ethyl und -natrium, Mecoprop, Mecoprop-nat um, Mecoprop-butotyl, Mecoprop-P-butotyl, Mecoprop-P-dimethylammonium, Mecoprop-P- 2-ethylhexyl, Mecoprop-P-kalium, Mefenacet, Mefluidide, Mepiquat-chlorid, Isoxachlortole, Isoxaflutole, Isoxapyrifop, KUH-043, ie 3 - ({[5- (difluoromethyl) -1-methyl-3- (thfluoromethyl) -1H-pyrazol-4-yl] methyl} sulfonyl) -5,5- dinethyl-4,5-dihydro-1, 2-oxazole, carbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecopropate, mecopropbutotyl , Mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P 2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidides, mepiquat chloride,
Mesosulfuron, Mesosulfuron-methyl, Mesotrione, Methabenzthiazuron, Metam, Mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam,
Metamifop, Metamitron, Metazachlor, Metazasulfuron, Methazole, Methiopyrsulfuron, Methiozolin, Methoxyphenone, Methyldymron, 1 -Methylcyclopropen, Metamifop, metamitron, metazachlor, metazasulfuron, methazole, methiopyrsulfuron, methiozoline, methoxyphenones, methyldymron, 1-methylcyclopropene,
Methylisothiocyanat, Metobenzuron, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron, Metsulfuron-methyl, Molinate, Methylisothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinates,
Monalide, Monocarbamide, Monocarbamide-dihydrogensulfat, Monolinuron, Monalides, monocarbamides, monocarbamide dihydrogen sulfate, monolinuron,
Monosulfuron, Monosulfuron-ester, Monuron, MT-128, d. h. 6-Chlor-N-[(2E)-3- chlorprop-2-en-1 -yl]-5-methyl-N-phenylpyridazin-3-annin, MT-5950, d. h. N-[3-Chlor-4- (1 -methylethyl)-phenyl]-2-nnethylpentanannid, NGGC-01 1 , Naproanilide, Napropamide, Naptalam, NC-310, d.h. 4-(2,4-Dichlorobenzoyl)-1 -methyl-5-benzyloxypyrazole, Neburon, Nicosulfuron, Nipyraclofen, Nitralin, Nitrofen, Nitrophenolat-nathum Monosulfuron, Monosulfuron Ester, Monuron, MT-128, d. H. 6-Chloro-N - [(2E) -3-chloroprop-2-en-1-yl] -5-methyl-N-phenylpyridazine-3-annine, MT-5950, d. H. N- [3-chloro-4- (1-methylethyl) -phenyl] -2-methylpentanannide, NGGC-01 1, naproanilides, napropamide, naptalam, NC-310, i. 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazoles, neburon, nicosulfuron, nipyraclofen, nitrite, nitrofen, nitrophenolate nathum
(Isomerengemisch), Nitrofluorfen, Nonansäure, Norflurazon, Orbencarb, (Mixture of isomers), nitrofluorfen, nonanoic acid, norflurazon, orbencarb,
Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paclobutrazol, Paraquat, Paraquat-dichlorid, Pelargonsäure Orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquat-dichloride, pelargonic acid
(Nonansäure), Pendimethalin, Pendralin, Penoxsulam, Pentanochlor, Pentoxazone, Perfluidone, Pethoxamid, Phenisopham, Phenmedipham, Phenmedipham-ethyl, Picloram, Picolinafen, Pinoxaden, Piperophos, Pirifenop, Pirifenop-butyl, Pretilachlor, Primisulfuron, Primisulfuron-methyl, Probenazole, Profluazol, Procyazine, Prodiamine, Prifluraline, Profoxydim, Prohexadione, Prohexadione-calcium, Prohydrojasmone, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-nathum, Propyrisulfuron,  (Nonanoic acid), pendimethalin, pendalkin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamide, phenisopham, phenmedipham, phenmediphamethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenoputyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazoles, Profluazole, Procyazine, Prodiamine, Prifluralin, Profoxydim, Prohexadione, Prohexadione-calcium, Prohydrojasmone, Prometon, Prometry, Propachlor, Propanil, Propaquizafop, Propazine, Propam, Propisochlor, Propoxycarbazone, Propoxycarbazone-nathum, Propyrisulfuron,
Propyzannide, Prosulfalin, Prosulfocarb, Prosulfuron, Prynachlor, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolynate (Pyrazolate), Pyrazosulfuron, Propyzannide, Prosulfine, Prosulfocarb, Prosulfuron, Prynachlor, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolynate (Pyrazolate), Pyrazosulfuron,
Pyrazosulfuron-ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-isopropyl, Pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl,
Pyribambenz-propyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridate, Pyriftalid,  Pyribambenz-propyl, Pyribenzoxime, Pyributicarb, Pyridafol, Pyridate, Pyriftalid,
Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac-natrium, Pyroxasulfone, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsulfuron, Saflufenacil, Secbumeton, Sethoxydim, Siduron, Simazine, Simetryn, SN-106279, d. h. Methyl-(2R)-2-({7-[2-chlor-4-(trifluormethyl)phenoxy]-2-naphthyl}oxy)propanoat, Sulcotrione, Sulfallate (CDEC), Sulfentrazone, Sulfometuron, Sulfometuron-methyl, Sulfosate (Glyphosate-trimesium), Sulfosulfuron, SYN-523, SYP-249, d. h. 1 -Ethoxy-3- methyl-1 -oxobut-3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP- 300, d. h. 1 -[7-Fluor-3-oxo-4-(prop-2-in-1 -yl)-3,4-dihydro-2H-1 ,4-benzoxazin-6-yl]-3- propyl-2-thioxoimidazolidin-4,5-dion, Tebutam, Tebuthiuron, Tecnazene, Tefuryltrione, Tembotrione, Tepraloxydim, Terbacil, Terbucarb, Terbuchlor, Terbumeton, Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac Sodium, Pyroxasulfones, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsulfuron, Saflufenacil, Secbumetone, sethoxydim, siduron, simazine, simetryn, SN-106279, ie methyl (2R) -2- ({7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthyl} oxy) propanoate, sulcotrione, Sulphates (CDEC), sulphentrazone, sulphometuron, sulphometuron-methyl, sulphosate (glyphosate-trimesium), sulphosulphuron, SYN-523, SYP-249, ie 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl -5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP- 300, ie 1 - [7-fluoro-3-oxo-4- (prop-2-yn-1-yl) -3,4-dihydro-2H-1,4-benzoxazin-6-yl] -3-propyl -2-thioxoimidazolidine-4,5-dione, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,
Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazafluron, Thiazopyr, Thidiazimin, Thidiazuron, Thiencarbazone, Thiencarbazone-methyl, Thifensulfuron, Thifensulfuron-methyl, Thiobencarb, Tiocarbazil, Topramezone, Tralkoxydim, Terbuthylazines, terbutryn, thenylchloro, thiafluamides, thiazafluron, thiazopyr, thidiazimine, thidiazuron, thiencarbazones, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, toramezone, tralkoxydim,
Triafamon, Triallate, Triasulfuron, Triaziflam, Triazofenamide, Tribenuron, Tribenuron- methyl, Trichloressigsäure (TCA), Triclopyr, Tridiphane, Trietazine, Trifloxysulfuron, Trifloxysulfuron-natrium, Trifluralin, Triflusulfuron, Triflusulfuron-methyl, Trimeturon, Trinexapac, Trinexapac-ethyl, Tritosulfuron, Tsitodef, Uniconazole, Uniconazole-P, Vernolate, ZJ-0862, d. h. 3,4-Dichlor-N-{2-[(4,6-dimethoxypyrimidin-2- yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: Triafamon, triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuronmethyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron , Tsitodef, Uniconazole, Uniconazole-P, Vernolate, ZJ-0862, d. H. 3,4-Dichloro-N- {2 - [(4,6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following compounds:
Figure imgf000031_0001
Figure imgf000031_0001
Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare For use, the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dusty preparations, ground or spreading granules and sprayable
Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids, u.a. variiert die erforderliche Aufwandmenge der Solutions are usually no longer with inert before use Diluted substances. With the external conditions such as temperature, humidity, the type of herbicide used, etc. varies the required application rate of
Verbindungen der Formel (I). Sie kann innerhalb weiter Grenzen schwanken, z.B. zwischen 0,001 und 1 ,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,005 und 750 g/ha. Compounds of the formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
Die nachstehenden Beispiele erläutern die Erfindung. The following examples illustrate the invention.
A. Chemische Beispiele A. Chemical examples
1 . Synthese von 2-Chlor-4-(methylsulfonyl)-N-(1 -(2-methoxyethyl)-tetrazol-5-yl)- benzamid, (Tabellenbeispiel Nr. 1 -12)  1 . Synthesis of 2-chloro-4- (methylsulfonyl) -N- (1- (2-methoxyethyl) -tetrazol-5-yl) -benzamide (Table Example No. 1-12)
176 mg (0.75 mmol) 2-Chlor-4-(methylsulfonyl)-benzoylchlorid, 145 mg (1 .0 mmol) 5- Amino-1 -(2-methoxyethyl)-tetrazol in 2 ml Pyridin werden 12 h bei 60°C gerührt.  176 mg (0.75 mmol) of 2-chloro-4- (methylsulfonyl) benzoyl chloride, 145 mg (1 .0 mmol) of 5-amino-1- (2-methoxyethyl) -tetrazole in 2 ml of pyridine are heated at 60 ° C. for 12 h touched.
Anschließend werden 0.1 ml Wasser zugegeben, 30 min. bei 60°C gerührt und mit EE und 2N HCl versetzt. Die abgetrennte organische Phase wird nochmals mit 2N HCl und Kochsalzlösung gewaschen, über Na2SO4 getrocknet, eingedampft und mittels RP-HPLC (Aceton it l/Wassser) gereinigt. Ausbeute 66 mg (23%). Synthese von 5-Amino-1 -(2-methoxyethyl)-tetrazol Subsequently, 0.1 ml of water are added, 30 min. stirred at 60 ° C and treated with EA and 2N HCl. The separated organic phase is again washed with 2N HCl and brine, dried over Na 2 SO 4 , evaporated and purified by RP-HPLC (acetone it l / Wassser). Yield 66 mg (23%). Synthesis of 5-amino-1- (2-methoxyethyl) tetrazole
Eine Mischung von 2.33 g (10 mmol) S-Methyl-isothiosemicarbazid-hydroiodid und 751 mg (10 mmol) 2-Methoxyethylamin werden in 10 ml Ethanol solange unter Rückfluß erhitzt, bis kein Methlmercaptan mehr freigesetzt wird. Anschließend wird  A mixture of 2.33 g (10 mmol) of S-methylisothiosemicarbazide hydroiodide and 751 mg (10 mmol) of 2-methoxyethylamine are refluxed in 10 ml of ethanol until no more mercaptancaptan is liberated. Subsequently, will
weitestgehend eingeengt, nacheinander unter Rühren mit 10 ml Wasser, 0.3 ml konz. Salpetersäure und 1 .7 g (10 mmol) Silbernitrat in 2 ml Wasser versetzt. Nach 10 min Rühren versetzt man mit 0.5 ml konz. Salzsäure, saugt den Niederschlag ab, wäscht mit 3 ml Wasser und versetzt das Filtrat mit 1 .5 ml konz. Salzsäure. Die Mischung wird bei <5°C mit 0.7 g (10 mmol) Natriumnitrit in 2 ml Wasser versetzt und anschließend mit 20 %iger Natronlauge auf pH 10 eingestellt. Anschließend wird 30 min auf 60 °C erhitzt und nach dem Abkühlen mit Essigester extrahiert. Die org. Phase wird 3x mit ges. Kochsalzlösung gewaschen, getrocknet, eingeengt und der Rückstand mit wenig Essigester aufgenommen und filtriert. Beige Kristalle, Ausbeute 590 mg (40%). NMR (DMSO-de): 6.62 (brs,2H), 4.26 (t,2H), 3.65 (t,2H), 3.23 (s,3H) Tabelle 1 : Erfindungsgemäße Verbindungen der Formel (I), worin A für CY, B für N und R für 2-Methoxyethyl stehtconcentrated as far as possible, successively with stirring with 10 ml of water, 0.3 ml of conc. Nitric acid and 1 .7 g (10 mmol) of silver nitrate in 2 ml of water. After stirring for 10 minutes, 0.5 ml of conc. Hydrochloric acid, the precipitate is filtered off with suction, washed with 3 ml of water and the filtrate is combined with 1 .5 ml of conc. Hydrochloric acid. The mixture is mixed at <5 ° C with 0.7 g (10 mmol) of sodium nitrite in 2 ml of water and then adjusted to pH 10 with 20% sodium hydroxide solution. The mixture is then heated for 30 min at 60 ° C and extracted after cooling with ethyl acetate. The org. Phase is 3x with sat. Washed brine, dried, concentrated and the residue taken up with a little ethyl acetate and filtered. Beige crystals, yield 590 mg (40%). NMR (DMSO-de): 6.62 (brs, 2H), 4.26 (t, 2H), 3.65 (t, 2H), 3.23 (s, 3H) Table 1: Compounds of the invention of the formula (I) wherein A is CY, B is N and R is 2-methoxyethyl
Figure imgf000033_0001
Nr. X Y Z Physikalische Daten
Figure imgf000033_0001
No. XYZ Physical Data
( H-NMR, DMSO-d6,400 MHz)-24 Cl H 4-Methyl-3- trifluormethyl- 1,2,4-triazolin-5- οη-1-yl(H-NMR, DMSO-d 6 , 400 MHz) -24 Cl H 4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-o-1-yl
-25 Br H F-25 Br H F
-26 Br H Cl 9.79 (bs,1H), 7.68-7.64 (m,2H), -26 Br H Cl 9.79 (bs, 1H), 7.68-7.64 (m, 2H),
7.45 (dd,1H), 4.63 (t,2H), 3.83 (t,2H), 3.36 (s,3H) 7.45 (dd, 1H), 4.63 (t, 2H), 3.83 (t, 2H), 3.36 (s, 3H)
-27 Br H Br-27 Br H Br
-28 Br H SMe 9.8 (bs,1H), 7.65 (d,1H), 7.45 -28 Br H SMe 9.8 (bs, 1H), 7.65 (d, 1H), 7.45
(d,1H), 7.26 (dd,1H), 4.65 (t,2H), 3.84 (t,2H), 3.36 (s,3H), 2.52 (s,3H) (d, 1H), 7.26 (dd, 1H), 4.65 (t, 2H), 3.84 (t, 2H), 3.36 (s, 3H), 2.52 (s, 3H)
-29 Br H S02Me-29 Br H S0 2 Me
-30 Br H S02Et-30 Br H S0 2 Et
-31 Br H CF3 -31 Br H CF 3
-32 OMe H S02Me-32 OMe H S0 2 Me
-33 SMe H F-33 SMe H F
-34 SMe H Cl 10.65 (bs,1H), 7.83 (d,1H), 7.31 -34 SMe H Cl 10.65 (bs, 1H), 7.83 (d, 1H), 7.31
(d,1H), 7.28 (dd,1H), 4.63 (t,2H), 3.83 (t,2H), 3.34 (s,3H), 2.49 (s,3H) (d, 1H), 7.28 (dd, 1H), 4.63 (t, 2H), 3.83 (t, 2H), 3.34 (s, 3H), 2.49 (s, 3H)
-35 S02Me H Cl-35 S0 2 Me H Cl
-36 SMe H Br-36 SMe H Br
-37 S02Me H Br-37 S0 2 Me H Br
-38 SMe H SMe-38 SMe H SMe
-39 S02Me H SMe-39 S0 2 Me H SMe
-40 S02Me H SOMe-40 S0 2 Me H SOMe
-41 S02Me H S02Me-41 S0 2 Me H S0 2 Me
-42 SMe H CF3 10.6 (bs,1H), 7.95 (d,1H), 7.57 -42 SMe H CF 3 10.6 (bs, 1H), 7.95 (d, 1H), 7.57
(s,1H), 7.54 (d,1H), 4.67 (t,2H), 3.85 (t,2H), 3.34 (s,3H), 2.53 (s,3H) (s, 1H), 7.54 (d, 1H), 4.67 (t, 2H), 3.85 (t, 2H), 3.34 (s, 3H), 2.53 (s, 3H)
-43 SOMe H CF3 -43 SOMe H CF 3
-44 S02Me H CF3 8.18 (s,1H), 8.15 (d,1H), 7.97 -44 S0 2 Me H CF 3 8.18 (s, 1H), 8.15 (d, 1H), 7.97
(d,1H), 4.42 (m,2H), 3.71 (m,2H), 3.54 (s,3H), 3.21 (s,3H)-45 S02Et H Cl(d, 1H), 4.42 (m, 2H), 3.71 (m, 2H), 3.54 (s, 3H), 3.21 (s, 3H) -45 S0 2 EtH Cl
-46 S02Et H Br-46 S0 2 Et H Br
-47 S02Et H SMe-47 S0 2 Et H SMe
-48 S02Et H SOMe-48 S0 2 Et H SOMe
-49 S02Et H S02Me-49 S0 2 Et H S0 2 Me
-50 S02Et H CF3 -50 S0 2 Et H CF 3
-51 S02NMePh H Cl-51 S0 2 NMePh H Cl
-52 S02NMe2 H CF3
Figure imgf000035_0001
MHz) -52 S0 2 NMe 2 H CF 3
Figure imgf000035_0001
MHz)
7.34
Figure imgf000036_0001
Figure imgf000037_0001
Nr. X Y Z Physikalische Daten 7:34
Figure imgf000036_0001
Figure imgf000037_0001
No. XYZ Physical Data
( H-NMR, DMSO-d6,400 MHz)-150 Me OMe Br 9.94 (bs,1H), 7.53 (d,1H), 7.27 (H-NMR, DMSO-d 6 , 400 MHz) -150 Me OMe Br 9.94 (bs, 1H), 7.53 (d, 1H), 7.27
(d,1H), 4.62 (t,2H), 3.85 (s,3H), 3.83 (t,2H), 3.34 (s,3H), 3.22 (s,3H), 2.51 (s,3H) (d, 1H), 4.62 (t, 2H), 3.85 (s, 3H), 3.83 (t, 2H), 3.34 (s, 3H), 3.22 (s, 3H), 2.51 (s, 3H)
-151 Me OEt Br-151 Me OEt Br
-152 Me 0(CH2)2OMe Br 9.86 (bs,1H), 7.52 (d,1H), 7.25 -152 Me 0 (CH 2 ) 2 OMe Br 9.86 (bs, 1H), 7.52 (d, 1H), 7.25
(d,1H), 4.62 (t,2H), 4.10 (t,2H), 3.84-3.78 (m,4H), 3.47 (s,3H), 3.36 (s,3H), 2.53 (s,3H)-153 Me 0(CH2)3OMe Br 9.81 (bs,1H), 7.52 (d,1H), 7.24 (d, 1H), 4.62 (t, 2H), 4.10 (t, 2H), 3.84-3.78 (m, 4H), 3.47 (s, 3H), 3.36 (s, 3H), 2.53 (s, 3H) - 153 Me 0 (CH 2 ) 3 OMe Br 9.81 (bs, 1H), 7.52 (d, 1H), 7.24
(d,1H), 4.61 (t,2H), 4.01 (t,2H), 3.83 (t,2H), 3.65 (t,2H), 3.38 (s,3H), 3.35 (s,3H), 2.50 (s,3H), 2.13 (m,2H) (d, 1H), 4.61 (t, 2H), 4.01 (t, 2H), 3.83 (t, 2H), 3.65 (t, 2H), 3.38 (s, 3H), 3.35 (s, 3H), 2.50 ( s, 3H), 2.13 (m, 2H)
-154 Me 0(CH2)2SMe Br 11.46 (bs,1H), 7.65 (d,1H), 7.32 -154 Me 0 (CH 2 ) 2 SMe Br 11.46 (bs, 1H), 7.65 (d, 1H), 7.32
(d,1H), 4.54 (t,2H), 4.05 (t,2H), 3.75 (t,2H), 3.22 (s,3H), 2.93 (t,2H), 2.41 (s,3H), 2.17 (s,3H)-155 Me 0(CH2)2SEt Br 11.45 (bs,1H), 7.65 (d,1H), 7.32 (d, 1H), 4.54 (t, 2H), 4.05 (t, 2H), 3.75 (t, 2H), 3.22 (s, 3H), 2.93 (t, 2H), 2.41 (s, 3H), 2.17 ( s, 3H) -155 Me 0 (CH 2 ) 2 SEt Br 11.45 (bs, 1H), 7.65 (d, 1H), 7.32
(d,1H), 4.54 (t,2H), 4.03 (t,2H), 3.75 (t,2H), 3.22 (s,3H), 2.96 (t,2H), 2.63 (q,2H), 2.41 (s,3H), 1.22 (t,3H) (d, 1H), 4.54 (t, 2H), 4.03 (t, 2H), 3.75 (t, 2H), 3.22 (s, 3H), 2.96 (t, 2H), 2.63 (q, 2H), 2.41 ( s, 3H), 1.22 (t, 3H)
-156 Me 0(CH2)3SMe Br-156 Me 0 (CH 2 ) 3 SMe Br
-157 Me OCH2CONMe2 Br 10.32 (bs,1H), 7.49 (d,1H), 7.32 -157 Me OCH 2 CONMe 2 Br 10.32 (bs, 1H), 7.49 (d, 1H), 7.32
(d,1H), 4.62 (t,2H), 4.57 (s,2H), 3.83 (t,2H), 3.35 (s,3H), 3.05 (s,3H), 3.01 (s,3H), 2.38 (s,3H)-158 Me 0(CH2)-5-pyrrolidin-2-on Br(d, 1H), 4.62 (t, 2H), 4.57 (s, 2H), 3.83 (t, 2H), 3.35 (s, 3H), 3.05 (s, 3H), 3.01 (s, 3H), 2.38 ( s, 3H) -158 Me 0 (CH 2 ) -5-pyrrolidin-2-one Br
-159 Me SMe Br-159 Me SMe Br
-160 Me SOMe Br-160 Me SOMe Br
-161 Me S02Me Br-161 Me S0 2 Me Br
-162 Me SEt Br 9.22 (bs,1H), 7.64 (d,1H), 7.28 -162 Me SE Br 9.22 (bs, 1H), 7.64 (d, 1H), 7.28
(d,1H), 4.60 (t,2H), 3.82 (t,2H), 3.35 (s,3H), 2.88 (q,2H), 2.79 (s,3H), 1.24 (t,3H) (d, 1H), 4.60 (t, 2H), 3.82 (t, 2H), 3.35 (s, 3H), 2.88 (q, 2H), 2.79 (s, 3H), 1.24 (t, 3H)
-163 Me SOEt Br 9.60 (bs,1H), 7.56 (d,1H), 7.41 -163 Me SOEt Br 9.60 (bs, 1H), 7.56 (d, 1H), 7.41
(d,1H), 4.60 (t,2H), 3.82 (t,2H), 3.35 (s,3H), 3.29-3.34 (m,1H), 3.10-3.15 (m,1H), 2.82 (s,3H), 1.42 (t,3H) (d, 1H), 4.60 (t, 2H), 3.82 (t, 2H), 3.35 (s, 3H), 3.29-3.34 (m, 1H), 3.10-3.15 (m, 1H), 2.82 (s, 3H ), 1.42 (t, 3H)
-164 Me S02Et Br 9.38 (bs,1H), 7.78 (d,1H), 7.46 -164 Me S0 2 Et Br 9.38 (bs, 1H), 7.78 (d, 1H), 7.46
(bs,1H), 4.60 (t,2H), 3.82 (t,2H), 3.50 (q,2H), 3.37 (s,3H), 2.85 (s,3H), 1.39 (t,3H) (bs, 1H), 4.60 (t, 2H), 3.82 (t, 2H), 3.50 (q, 2H), 3.37 (s, 3H), 2.85 (s, 3H), 1.39 (t, 3H)
-165 Me SMe I-165 Me SMe I
-166 Me SOMe I-166 Me SOMe I
-167 Me S02Me I-167 Me S0 2 Me I
-168 Me SEt I Nr. X Y Z Physikalische Daten -168 Me SEt I No. XYZ Physical Data
( H-NMR, DMSO-d6, 400 MHz)-169 Me SOEt I(H-NMR, DMSO-d 6 , 400 MHz) -169 Me SOEt I
-170 Me S02Et I-170 Me S0 2 Et I
-171 Me Cl CF3 9.95 (brs, 1 H), 7.68 (d,H), 7.56 -171 Me Cl CF 3 9.95 (brs, 1H), 7.68 (d, H), 7.56
(d, 1 H), 4.64 (t,2H), 3.83 (t,2H), 3.36 (s,3H), 2.59 (s,3H)-172 Me SMe CF3 7.74 (d,H), 7.68 (d, 1 H), 4.48 (d, 1H), 4.64 (t, 2H), 3.83 (t, 2H), 3.36 (s, 3H), 2.59 (s, 3H) -172 Me SMe CF 3 7.74 (d, H), 7.68 (i.e. , 1H), 4.48
(m,2H), 3.74 (m,2H), 3.22 (s,3H), 2.70 (s,3H), 2.30 (s,3H)-173 Me SOMe CF3 7.90 (s,2H), 4.59 (t,2H), 3.76 (m, 2H), 3.74 (m, 2H), 3.22 (s, 3H), 2.70 (s, 3H), 2.30 (s, 3H) -173 Me SOMe CF 3 7.90 (s, 2H), 4.59 (t, 2H), 3.76
(t,2H), 3.24 (s,3H), 3.06 (s,3H), 2.88 (s,3H) (t, 2H), 3.24 (s, 3H), 3.06 (s, 3H), 2.88 (s, 3H)
-174 Me S02Me CF3 7.89 (d,1 H), 7.82 (d, 1 H), 4.37 -174 Me S0 2 Me CF 3 7.89 (d, 1 H), 7.82 (d, 1 H), 4.37
(m,2H), 3.71 (m,2H), 3.37 (s,3H), 3.22 (s,3H), 2.75 (s,3H)-175 Me SEt CF3 (m, 2H), 3.71 (m, 2H), 3.37 (s, 3H), 3.22 (s, 3H), 2.75 (s, 3H) -175 Me SEt CF 3
-176 Me SOEt CF3 -176 Me SOEt CF 3
-177 Me S02Et CF3 -177 Me S0 2 Et CF 3
-178 Me S(CH2)2OMe CF3 -178 Me S (CH 2 ) 2 OMe CF 3
-179 Me S(0)(CH2)2OMe CF3 -179 Me S (0) (CH 2 ) 2 OMe CF 3
-180 Me S02(CH2)2OMe CF3 -180 Me S0 2 (CH 2 ) 2 OMe CF 3
-181 Me SMe OMe-181 Me SMe OMe
-182 Me SOMe OMe-182 Me SOMe OMe
-183 Me S02Me OMe-183 Me S0 2 Me OMe
-184 Me SEt OMe-184 Me SEt OMe
-185 Me SOEt OMe-185 Me SOEt OMe
-186 Me S02Et OMe-186 Me S0 2 Et OMe
-187 Me Me SMe 9.75 (brs,1 H), 7.45 (d, 1 H), 7.08 -187 Me Me SMe 9.75 (brs, 1H), 7.45 (d, 1H), 7.08
(d, 1 H), 4.63 (t,2H), 3.83 (t,2H), 3.35 (s,1 H), 2.50 (s,3H), 2.46 (s,3H), 2.32 (s,3H) (d, 1H), 4.63 (t, 2H), 3.83 (t, 2H), 3.35 (s, 1H), 2.50 (s, 3H), 2.46 (s, 3H), 2.32 (s, 3H)
-188 Me Me S02Me 9.90 (brs, 1 H), 8.02 (d, 1 H), 7.51 -188 Me Me S0 2 Me 9.90 (brs, 1 H), 8.02 (d, 1 H), 7.51
(d, 1 H), 4.64 (t,2H), 3.83 (t,2H), 3.35 (s,1 H), 3.13 (s,3H), 2.70 (s,3H), 2.48 (s,3H) (d, 1H), 4.64 (t, 2H), 3.83 (t, 2H), 3.35 (s, 1H), 3.13 (s, 3H), 2.70 (s, 3H), 2.48 (s, 3H)
-189 Me Me SEt-189 Me Me SEt
-190 Me Me S02Et-190 Me Me S0 2 Et
-191 Me 4,5-dihydro-1 ,2-oxazol-3 S02Me -191 Me 4,5-dihydro-1,2-oxazol-3 S0 2 Me
yi yi
-192 Me 4,5-dihydro-1 ,2-oxazol-3 S02Et -192 Me 4,5-dihydro-1,2-oxazole-3SO 2 Et
yi yi
-193 Me 5-cyanomethyl- 4,5- S02Me -193 Me 5-cyanomethyl-4,5-S0 2 Me
dihydro-1 ,2-oxazol-3-yl dihydro-1,2-oxazol-3-yl
-194 Me 5-cyanomethyl- 4,5- S02Et -194 Me 5-cyanomethyl-4,5-S0 2 Et
dihydro-1 ,2-oxazol-3-yl dihydro-1,2-oxazol-3-yl
-195 Me NH2 S02Me Nr. X Y Z Physikalische Daten -195 Me NH 2 S0 2 Me No. XYZ Physical Data
( H-NMR, DMSO-d6,400 MHz)-196 Me NHMe S02Me(H-NMR, DMSO-d 6 , 400 MHz) -196 Me NHMe S0 2 Me
-197 Me NMe2 S02Me 9.95 (brs,1H), 7.99 (d,1H), 7.51 -197 Me NMe2 S0 2 Me 9.95 (brs, 1H), 7.99 (d, 1H), 7.51
(d,1H), 4.64 (t,2H), 3.84 (t,2H), 3.37 (s,1H), 3.27 (s,3H), 2.92 (s,6H), 2.50 (s,3H) (d, 1H), 4.64 (t, 2H), 3.84 (t, 2H), 3.37 (s, 1H), 3.27 (s, 3H), 2.92 (s, 6H), 2.50 (s, 3H)
-198 Me NHEt S02Me-198 Me NHEt S0 2 Me
-199 Me NHnPr S02Me-199 Me NHnPr S0 2 Me
-200 Me NHiPr S02Me 9.87 (brs,1H), 7.80 (d,1H), 7.12 -200 Me NHiPr S0 2 Me 9.87 (brs, 1H), 7.80 (d, 1H), 7.12
(d,1H), 4.64 (t,2H), 3.83 (t,2H), 3.77 (sept,1H), 3.36 (s,1H), 3.11 (s,3H), 2.41 (s,3H), 1.22 (d,6H) (d, 1H), 4.64 (t, 2H), 3.83 (t, 2H), 3.77 (sept, 1H), 3.36 (s, 1H), 3.11 (s, 3H), 2.41 (s, 3H), 1.22 ( d, 6H)
-201 Me NHcPr S02Me 9.71 (brs,1H), 7.75 (d,1H), 7.06 -201 Me NHcPr S0 2 Me 9.71 (brs, 1H), 7.75 (d, 1H), 7.06
(d,1H), 6.25 (bs,1H), 4.64 (t,2H), 3.83 (t,2H), 3.36 (s,1H), 3.00 (s,3H), 2.84 (m,1H), 2.60 (s,3H), 0.81 (m,2H), 0.61 (m,2H) (d, 1H), 6.25 (bs, 1H), 4.64 (t, 2H), 3.83 (t, 2H), 3.36 (s, 1H), 3.00 (s, 3H), 2.84 (m, 1H), 2.60 ( s, 3H), 0.81 (m, 2H), 0.61 (m, 2H)
-202 Me NHiBu S02Me-202 Me NHiBu S0 2 Me
-203 Me NHCH2cPr S02Me-203 Me NHCH 2 cPr S0 2 Me
-204 Me NH(CH2)2OMe S02Me 9.95 (bs, 1H), 7.81 (d, 1H), 7.15 -204 Me NH (CH 2 ) 2 OMe SO 2 Me 9.95 (bs, 1H), 7.81 (d, 1H), 7.15
(d, 1H), 4.64 (t, 2H), 3.84 (t, 2H), 3.60 (t, 2H), 3.42 (t, 2H), 3.40 (s, 3H), 3.36 (s, 3H), 3.20 (s,3H), 2.43 (s, 3H) (d, 1H), 4.64 (t, 2H), 3.84 (t, 2H), 3.60 (t, 2H), 3.42 (t, 2H), 3.40 (s, 3H), 3.36 (s, 3H), 3.20 ( s, 3H), 2.43 (s, 3H)
-205 Me NH(CH2)2OEt S02Me-205 Me NH (CH 2 ) 2 OEt S0 2 Me
-206 Me NH(CH2)3OMe S02Me-206 Me NH (CH 2 ) 3 OMe S0 2 Me
-207 Me NHCH2CH(OMe)Me S02Me-207 Me NHCH 2 CH (OMe) Me S0 2 Me
-208 Me NHCH2CH(OMe)CH2OMe S02Me-208 Me NHCH 2 CH (OMe) CH 2 OMe S0 2 Me
-209 Me NH(CH2)3OEt S02Me-209 Me NH (CH 2 ) 3 OEt S0 2 Me
-210 Me NHCH2-tetrahyd rof u ran-2- S02Me 9.91 (bs,1H), 7.81 (d,1H), 7.15 yi (d,1H), 4.64 (t,2H), 4.15 (m,1H), -210M NHCH 2 -tetrahydrofuran- 2- SO 2 Me 9.91 (bs, 1H), 7.81 (d, 1H), 7.15 yi (d, 1H), 4.64 (t, 2H), 4.15 (m, 1H )
3.91 (dd,1H), 3.84 (t,2H), 3.79 (dd,1H), 3.43 (dd,1H), 3.36 (s,3H), 3.24 (s,3H), 3.18 (dd,1H), 2.43 (s,3H), 2.09-1.90 (m,3H), 1.72-1.63 (m,1H)-211 Me NHCH2-(4-Me- S02Me 3.91 (dd, 1H), 3.84 (t, 2H), 3.79 (dd, 1H), 3.43 (dd, 1H), 3.36 (s, 3H), 3.24 (s, 3H), 3.18 (dd, 1H), 2.43 (s, 3H), 2.09-1.90 (m, 3H), 1.72-1.63 (m, 1H) -211 Me NHCH 2 - (4-Me-SO 2 Me
[1,3]dioxolan-2-yl) [1,3] dioxolan-2-yl)
-212 Me NH(CH2)2-(4-Me- S02Me -212 Me NH (CH 2 ) 2 - (4-Me- S0 2 Me
[1,3]dioxolan-2-yl) [1,3] dioxolan-2-yl)
-213 Me NHCH2-[1,3]dioxan-2-yl S02Me-213 Me NHCH 2 - [1,3] dioxan-2-yl SO 2 Me
-214 Me NHCH2CONHEt S02Me-214 Me NHCH 2 CONHEt S0 2 Me
-215 Me Pyrazol-1-yl S02Me 11.80 (brs,1H), 8.11 (d,1H), -215 Me pyrazol-1-yl SO 2 Me 11.80 (brs, 1H), 8.11 (d, 1H),
8.01 (d,1H), 7.99 (d,1H), 7.88 (d,1H), 6.59 (t,1H), 4.58 (t,2H), 3.77 (t,2H), 3.22 (s,3H), 3.05 (s,3H), 1.90 (s,3H) Nr. X Y Z Physikalische Daten 8.01 (d, 1H), 7.99 (d, 1H), 7.88 (d, 1H), 6.59 (t, 1H), 4.58 (t, 2H), 3.77 (t, 2H), 3.22 (s, 3H), 3.05 (s, 3H), 1.90 (s, 3H) No. XYZ Physical Data
( H-NMR, DMSO-d6, 400 MHz)-216 Me 3,5-Me2-Pyrazol-1-yl S02Me(H-NMR, DMSO-d 6 , 400 MHz) -216 Me 3,5-Me2-pyrazol-1-yl SO 2 Me
-217 Me 1 ,2,3-TriazoM-yl S02Me-217 Me 1, 2,3-triazoM-yl SO 2 Me
-218 Me 1 ,2,4-Triazol-1-yl S02Me-218 Me 1, 2,4-triazol-1-yl SO 2 Me
-219 Me OH S02Me-219 Me OH S0 2 Me
-220 Me OMe S02Me 10.2 (brs,1 H), 7.91 (d, 1 H), 7.50 -220 Me OMe S0 2 Me 10.2 (brs, 1 H), 7.91 (d, 1 H), 7.50
(d, 1 H), 4.65 (t,2H), 3.98 (s,1 H), 3.84 (t,2H), 3.37 (s,3H), 3.26 (s,3H), 2.53 (s,3H) (d, 1H), 4.65 (t, 2H), 3.98 (s, 1H), 3.84 (t, 2H), 3.37 (s, 3H), 3.26 (s, 3H), 2.53 (s, 3H)
-221 Me OMe S02Et-221 Me OMe S0 2 Et
-222 Me OEt S02Me-222 Me OEt S0 2 Me
-223 Me OEt S02Et-223 Me OEt S0 2 Et
-224 Me OiPr S02Me-224 Me OiPr S0 2 Me
-225 Me OiPr S02Et-225 Me OiPr S0 2 Et
-226 Me 0(CH2)2OMe S02Me-226 Me 0 (CH 2 ) 2 OMe S0 2 Me
-227 Me 0(CH2)2OMe S02Et-227 Me 0 (CH 2 ) 2 OMe S0 2 Et
-228 Me 0(CH2)3OMe S02Me-228 Me 0 (CH 2 ) 3 OMe S0 2 Me
-229 Me 0(CH2)3OMe S02Et-229 Me 0 (CH 2 ) 3 OMe S0 2 Et
-230 Me 0(CH2)4OMe S02Me-230 Me 0 (CH 2 ) 4 OMe S0 2 Me
-231 Me 0(CH2)4OMe S02Et-231 Me 0 (CH 2 ) 4 OMe S0 2 Et
-232 Me 0(CH2)2SMe S02Me-232 Me 0 (CH 2 ) 2 SMe S0 2 Me
-233 Me 0(CH2)2SEt S02Me-233 Me 0 (CH 2 ) 2 SEt S0 2 Me
-234 Me 0(CH2)3SMe S02Me-234 Me 0 (CH 2 ) 3 SMe S0 2 Me
-235 Me 0(CH2)2NHS02Me S02Me-235 Me 0 (CH 2 ) 2 NHS02Me S0 2 Me
-236 Me 0(CH2)2NHS02Me S02Et-236 Me 0 (CH 2 ) 2 NHSO 2 Me SO 2 Et
-237 Me OCH2(CO)NMe2 S02Me 10.5 (brs,1 H), 7.94 (d, 1 H), 7.55 -237 Me OCH 2 (CO) NMe 2 S0 2 Me 10.5 (brs, 1H), 7.94 (d, 1H), 7.55
(d, 1 H), 4.82 (s,2H), 4.67 (t,2H), 3.83 (t,2H), 3.40 (s,3H), 3.36 (s,3H), 3.04 (s,3H), 2.95 (s,3H), 2.53 (s,3H) (d, 1H), 4.82 (s, 2H), 4.67 (t, 2H), 3.83 (t, 2H), 3.40 (s, 3H), 3.36 (s, 3H), 3.04 (s, 3H), 2.95 (s, 3H), 2.53 (s, 3H)
-238 Me OCH2(CO)NMe2 S02Et-238 Me OCH 2 (CO) NMe 2 S0 2 Et
-239 Me OCH2-tetrahydrofuran-2-yl S02Me-239 Me OCH 2 -tetrahydrofuran-2-yl SO 2 Me
-240 Me OCH2-tetrahydrofuran-2-yl S02Et-240 Me OCH 2 -tetrahydrofuran-2-yl S0 2 Et
-241 Me [1 ,4]dioxan-2-yl-methoxy S02Me-241 Me [1,4] dioxan-2-ylmethoxy S0 2 Me
-242 Me [1 ,4]dioxan-2-yl-methoxy S02Et-242 Me [1,4] dioxan-2-yl-methoxy S0 2 Et
-243 Me F SMe-243 Me F SMe
-244 Me F S02Me-244 Me F S0 2 Me
-245 Me Cl S02Me 10.05 (brs,1 H), 8.1 1 (d,H), 7.61 -245 Me Cl S0 2 Me 10.05 (brs, 1 H), 8.1 1 (d, H), 7.61
(d, 1 H), 4.64 (t,2H), 3.84 (t,2H), 3.36 (s,3H), 3.32 (s,3H), 2.61 (s,3H) (d, 1H), 4.64 (t, 2H), 3.84 (t, 2H), 3.36 (s, 3H), 3.32 (s, 3H), 2.61 (s, 3H)
-246 Me SMe S02Me 7.99 (d,1 H), 7.74 (d, 1 H), 4.49 -246 Me SMe S0 2 Me 7.99 (d, 1 H), 7.74 (d, 1 H), 4.49
(t,2H), 3.74 (t,2H), 3.52 (s,3H), 3.23 (s,3H), 2.69 (s,3H), 2.38 (s,3H) Nr. X Y Z Physikalische Daten (t, 2H), 3.74 (t, 2H), 3.52 (s, 3H), 3.23 (s, 3H), 2.69 (s, 3H), 2.38 (s, 3H) No. XYZ Physical Data
( H-NMR, DMSO-d6, 400 MHz)-247 Me SOMe S02Me(H-NMR, DMSO-d 6 , 400 MHz) -247 Me SOMe S0 2 Me
-248 Me S02Me S02Me 1 1.80 (brs,1 H), 8.28 (d,1 H), -248 Me S0 2 Me S0 2 Me 1 1.80 (brs, 1 H), 8.28 (d, 1 H),
8.08 (d,1 H), 4.59 (t,2H), 3.77 (t,2H), 3.60 (s, 1 H), 3.58 (s,3H), 3.23 (s,3H), 2.72 (s,3H)-249 Me S02Me S02Et8.08 (d, 1H), 4.59 (t, 2H), 3.77 (t, 2H), 3.60 (s, 1H), 3.58 (s, 3H), 3.23 (s, 3H), 2.72 (s, 3H) -249 Me S0 2 Me S0 2 Et
-250 Me SEt S02Me-250 Me SEt S0 2 Me
-251 Me SOEt S02Me-251 Me SOEt S0 2 Me
-252 Me S02Et S02Me-252 Me S0 2 Et S0 2 Me
-253 Me S(CH2)2OMe S02Me-253 Me S (CH 2 ) 2 OMe S0 2 Me
-254 Me SO(CH2)2OMe S02Me-254 Me SO (CH 2 ) 2 OMe S0 2 Me
-255 Me S02(CH2)2OMe S02Me-255 Me S0 2 (CH 2 ) 2 OMe S0 2 Me
-256 CH2SMe OMe S02Me-256 CH 2 SMe OMe S0 2 Me
-257 CH2OMe OMe S02Me-257 CH 2 OMe OMe S0 2 Me
-258 CH20(CH2)20 NH(CH2)2OEt S02Me -258 CH 2 O (CH 2 ) 20 NH (CH 2 ) 2 OEt SO 2 Me
Me me
-259 CH20(CH2)20 NH(CH2)3OEt S02Me -259 CH 2 O (CH 2 ) 20 NH (CH 2 ) 3 OEt SO 2 Me
Me me
-260 CH20(CH2)30 OMe S02Me -260 CH 2 0 (CH 2 ) 3 0 OMe S0 2 Me
Me me
-261 CH20(CH2)20 NH(CH2)2OMe S02Me -261 CH 2 0 (CH 2 ) 2 0 NH (CH 2 ) 2 OMe SO 2 Me
Me me
-262 CH20(CH2)20 NH(CH2)3OMe S02Me -262 CH 2 0 (CH 2 ) 2 0 NH (CH 2 ) 3 OMe SO 2 Me
Me me
-263 Et NH(CH2)2OMe S02Me-263 Et NH (CH 2 ) 2 OMe S0 2 Me
-264 Et OMe S02Me-264 Et OMe S0 2 Me
-265 Et OMe S02Et-265 Et OMe S0 2 Et
-266 Et OEt S02Me-266 Et OEt S0 2 Me
-267 Et OEt S02Et-267 Et OEt S0 2 Et
-268 Et OiPr S02Me-268 Et OiPr S0 2 Me
-269 Et OiPr S02Et-269 Et OiPr S0 2 Et
-270 Et 0(CH2)2OMe S02Me-270 Et 0 (CH 2 ) 2 OMe S0 2 Me
-271 Et 0(CH2)2OMe S02Et-271 Et 0 (CH 2 ) 2 OMe S0 2 Et
-272 Et 0(CH2)3OMe S02Me-272 Et 0 (CH 2 ) 3 OMe S0 2 Me
-273 Et 0(CH2)3OMe S02Et-273 Et 0 (CH 2 ) 3 OMe S0 2 Et
-274 Et F S02Me-274 Et F S0 2 Me
-275 Et SMe Cl-275 Et SMe Cl
-276 Et SOMe Cl-276 Et SOMe Cl
-277 Et S02Me Cl-277 Et S0 2 Me Cl
-278 Et SMe Br-278 Et SMe Br
-279 Et SOMe Br-279 Et SOMe Br
-280 Et S02Me Br-280 Et S0 2 Me Br
-281 Et SMe I Nr. X Y Z Physikalische Daten -281 Et SMe I No. XYZ Physical Data
( H-NMR, DMSO-d6,400 MHz)-282 Et SOMe I(H-NMR, DMSO-d 6 , 400 MHz) -282 Et SOMe I
-283 Et S02Me I-283 Et S0 2 Me I
-284 Et SMe CF3 -284 Et SMe CF 3
-285 Et SOMe CF3 -285 Et SOMe CF 3
-286 Et S02Me CF3 -286 Et S0 2 Me CF 3
-287 Et SMe S02Me-287 Et SMe S0 2 Me
-288 Et SOMe S02Me-288 Et SOMe S0 2 Me
-289 Et S02Me S02Me-289 Et S0 2 Me S0 2 Me
-290 nPr SMe Cl-290 nPr SMe Cl
-291 nPr SOMe Cl-291 nPr SOMe Cl
-292 nPr S02Me Cl-292 nPr S0 2 Me Cl
-293 nPr SMe CF3 -293 nPr SMe CF 3
-294 nPr SOMe CF3 -294 nPr SOMe CF 3
-295 nPr S02Me CF3 -295 nPr S0 2 Me CF 3
-296 iPr SMe Cl-296 iPr SMe Cl
-297 iPr SOMe Cl-297 iPr SOMe Cl
-298 iPr S02Me Cl-298 iPr S0 2 Me Cl
-299 iPr SMe CF3 -299 iPr SMe CF 3
-300 iPr SOMe CF3 -300 iPr SOMe CF 3
-301 iPr S02Me CF3 -301 iPr S0 2 Me CF 3
-302 cPr SMe CF3 -302 cPr SMe CF 3
-303 cPr S02Me CF3 -303 cPr S0 2 Me CF 3
-304 CF3 0(CH2)2OMe F-304 CF 3 0 (CH 2 ) 2 OMe F
-305 CF3 0(CH2)3OMe F-305 CF 3 0 (CH 2 ) 3 OMe F
-306 CF3 OCH2CONMe2 F-306 CF 3 OCH 2 CONMe 2 F
-307 CF3 [1 ,4]dioxan-2-yl-methoxy F-307 CF 3 [1,4] dioxan-2-yl-methoxy F
-308 CF3 0(CH2)2OMe Cl-308 CF 3 0 (CH 2 ) 2 OMe Cl
-309 CF3 0(CH2)3OMe Cl-309 CF 3 0 (CH 2 ) 3 OMe Cl
-310 CF3 OCH2CONMe2 Cl-310 CF 3 OCH 2 CONMe 2 Cl
-311 CF3 [1 ,4]dioxan-2-yl-methoxy Cl-311 CF 3 [1,4] dioxan-2-ylmethoxy Cl
-312 CF3 0(CH2)2OMe Br-312 CF 3 O (CH 2 ) 2 OMe Br
-313 CF3 0(CH2)2OMe Br-313 CF 3 0 (CH 2 ) 2 OMe Br
-314 CF3 0(CH2)3OMe Br-314 CF 3 0 (CH 2 ) 3 OMe Br
-315 CF3 OCH2CONMe2 Br-315 CF 3 OCH 2 CONMe 2 Br
-316 CF3 [1 ,4]dioxan-2-yl-methoxy Br-316 CF 3 [1,4] dioxan-2-ylmethoxy Br
-317 CF3 0(CH2)2OMe I-317 CF 3 O (CH 2 ) 2 OMe I
-318 CF3 0(CH2)3OMe I-318 CF 3 O (CH 2 ) 3 OMe I
-319 CF3 OCH2CONMe2 I-319 CF 3 OCH 2 CONMe 2 I
-320 CF3 [1 ,4]dioxan-2-yl-methoxy I-320 CF 3 [1,4] dioxan-2-ylmethoxy I
-321 CF3 F S02Me Nr. X Y Z Physikalische Daten -321 CF 3 F S0 2 Me No. XYZ Physical Data
( H-NMR, DMSO-d6,400 MHz)-322 CF3 F S02Et(H-NMR, DMSO-d 6 , 400 MHz) -322 CF 3 F SO 2 Et
-323 CF3 0(CH2)2OMe S02Me-323 CF 3 O (CH 2 ) 2 OMe S0 2 Me
-324 CF3 0(CH2)2OMe S02Et-324 CF 3 O (CH 2 ) 2 OMe S0 2 Et
-325 CF3 0(CH2)3OMe S02Me-325 CF 3 O (CH 2 ) 3 OMe SO 2 Me
-326 CF3 0(CH2)3OMe S02Et-326 CF 3 0 (CH 2 ) 3 OMe S0 2 Et
-327 CF3 OCH2CONMe2 S02Me-327 CF 3 OCH 2 CONMe 2 S0 2 Me
-328 CF3 OCH2CONMe2 S02Et-328 CF 3 OCH 2 CONMe 2 S0 2 Et
-329 CF3 [1 ,4]dioxan-2-yl-methoxy S02Me-329 CF 3 [1,4] dioxan-2-ylmethoxy S0 2 Me
-330 CF3 [1 ,4]dioxan-2-yl-methoxy S02Et-330 CF 3 [1,4] dioxan-2-yl-methoxy S0 2 Et
-331 F SMe CF3 -331 F SMe CF 3
-332 F SOMe CF3 -332 F SOMe CF 3
-333 F S02Me CF3 -333 F S0 2 Me CF 3
-334 Cl SMe H-334 Cl SMe H
-335 Cl SOMe H-335 Cl SOMe H
-336 Cl S02Me H-336 Cl S0 2 Me H
-337 Cl SEt H-337 Cl SEt H
-338 Cl SOEt H-338 Cl SOEt H
-339 Cl S02Et H-339 Cl S0 2 Et H
-340 Cl S(CH2)2OMe H-340 Cl S (CH 2 ) 2 OMe H
-341 Cl SO(CH2)2OMe H-341 Cl SO (CH 2 ) 2 OMe H
-342 Cl S02(CH2)2OMe H-342 Cl S0 2 (CH 2 ) 2 OMe H
-343 Cl SMe Me 7.40-7.42 (m,1H), 7.08-7.10 -343 Cl SMe Me 7.40-7.42 (m, 1H), 7.08-7.10
(m,1H), 4.30-4.60 (m,2H), 3.70- 3.75 (m,2H), 3.35-3.50 (m,2H), 2.54 (s,3H), 2.29 (s,3H)-344 Cl SOMe Me 9.52 (bs,1H), 7.62 (d,1H), 7.30  (m, 1H), 4.30-4.60 (m, 2H), 3.70-3.75 (m, 2H), 3.35-3.50 (m, 2H), 2.54 (s, 3H), 2.29 (s, 3H) -344 Cl SOMe Me 9.52 (bs, 1H), 7.62 (d, 1H), 7.30
(d,1H), 4.60 (t,2H), 3.82 (t,2H), 3.37 (s,3H), 2.98 (s,3H), 2.78 (s,3H) (d, 1H), 4.60 (t, 2H), 3.82 (t, 2H), 3.37 (s, 3H), 2.98 (s, 3H), 2.78 (s, 3H)
-345 Cl S02Me Me 9.45 (bs,1H), 7.69 (d,1H), 7.39 -345 Cl S0 2 Me Me 9.45 (bs, 1H), 7.69 (d, 1H), 7.39
(d,1H), 4.59 (t,2H), 3.82 (t,2H), 3.40 (s,3H), 3.29 (s,3H), 2.83 (s,3H) (d, 1H), 4.59 (t, 2H), 3.82 (t, 2H), 3.40 (s, 3H), 3.29 (s, 3H), 2.83 (s, 3H)
-346 Cl SEt Me-346 Cl SEt Me
-347 Cl SOEt Me-347 Cl SOEt Me
-348 Cl S02Et Me-348 Cl S0 2 Et Me
-349 Cl Me Cl 9.71 (brs,1H), 7.49 (d,1H), 7.42 -349 Cl Me Cl 9.71 (brs, 1H), 7.49 (d, 1H), 7.42
(d,1H), 4.62 (t,2H), 3.83 (t,2H), 3.35 (s,3H), 2.53 (s,3H)-350 Cl CH2-pyrrolidin-2-on-1-yl Cl 9.8 (brs,1H), 7.60 (d,1H), 7.50 (d, 1H), 4.62 (t, 2H), 3.83 (t, 2H), 3.35 (s, 3H), 2.53 (s, 3H) -350 Cl CH 2 -pyrrolidin-2-one-1-yl Cl 9.8 (brs, 1H), 7.60 (d, 1H), 7.50
(d,1H), 4.83 (s,2H), 4.61 (t,2H), 3.83 (t,2H), 3.38 (s,1H), 3.13 (m,2H), 2.39 (m,2H), 1.96 (m,2H)
Figure imgf000045_0001
Nr. X Y Z Physikalische Daten (d, 1H), 4.83 (s, 2H), 4.61 (t, 2H), 3.83 (t, 2H), 3.38 (s, 1H), 3.13 (m, 2H), 2.39 (m, 2H), 1.96 ( m, 2H)
Figure imgf000045_0001
No. XYZ Physical Data
( H-NMR, DMSO-d6, 400 MHz)-373 Cl S02Me Cl(H-NMR, DMSO-d 6 , 400 MHz) -373 Cl SO 2 Me Cl
-374 Cl SEt Cl-374 Cl SEt Cl
-375 Cl SOEt Cl-375 Cl SOEt Cl
-376 Cl S02Et Cl-376 Cl S0 2 Et Cl
-377 Cl Me Br-377 Cl Me Br
-378 Cl CH2(4-Methyl-3- Br -378 Cl CH 2 (4-methyl-3-Br
isopropoxy-1 ,2,4-triazolin- 5-on-1-yl) isopropoxy-1,2,4-triazolin-5-one-1-yl)
-379 Cl CH2(4-Methyl-3- Br -379 Cl CH 2 (4-methyl-3-Br
trifluorethoxy-1 ,2,4- triazolin-5-on-1-yl) trifluoroethoxy-1, 2,4-triazolin-5-one-1-yl)
-380 Cl NHAc Br-380 Cl NHAc Br
-381 Cl NHCON(Me)OMe Br-381 Cl NHCON (Me) OMe Br
-382 Cl NHCH2CONHEt Br-382 Cl NHCH 2 CONHEt Br
-383 Cl NHCH2CONHiPr Br-383 Cl NHCH 2 CONHiPr Br
-384 Cl NHCHMeCONHEt Br-384 Cl NHCHMeCONHEt Br
-385 Cl OMe Br 9.49 (bs,1 H), 7.62 (d, 1 H), 7.40 -385 Cl OMe Br 9.49 (bs, 1 H), 7.62 (d, 1 H), 7.40
(d, 1 H), 4.60 (t,2H), 3.92 (s,3H), 3.82 (t,2H), 3.37 (s,3H),-386 Cl OEt Br (d, 1H), 4.60 (t, 2H), 3.92 (s, 3H), 3.82 (t, 2H), 3.37 (s, 3H), - 386 Cl OEt Br
-387 Cl OPr Br-387 Cl OPr Br
-388 Cl OAIIyl Br-388 Cl OAIIyl Br
-389 Cl OCH2CHF2 Br-389 Cl OCH 2 CHF 2 Br
-390 Cl 0(CH2)2OMe Br 1 1.71 (bs, 1 H), 7.81 (d, 1 H), 7.40 -390 Cl 0 (CH 2 ) 2 OMe Br 1 1.71 (bs, 1H), 7.81 (d, 1H), 7.40
(d, 1 H), 4.56 (t,2H), 4.24 (t,2H), 3.77 (t,2H), 3.74 (t,2H), 3.35 (s,3H), 3.23 (s,3H) (d, 1H), 4.56 (t, 2H), 4.24 (t, 2H), 3.77 (t, 2H), 3.74 (t, 2H), 3.35 (s, 3H), 3.23 (s, 3H)
-391 Cl 0(CH2)3OMe Br-391 Cl 0 (CH 2 ) 3 OMe Br
-392 Cl OCH2(CO)NMe2 Br-392 Cl OCH 2 (CO) NMe 2 Br
-393 Cl 0(CH2)-5-pyrrolidin-2-on Br-393 Cl 0 (CH 2 ) -5-pyrrolidin-2-one Br
-394 Cl Cl Br-394 Cl Cl Br
-395 Cl SMe Br-395 Cl SMe Br
-396 Cl SOMe Br-396 Cl SOMe Br
-397 Cl S02Me Br-397 Cl S0 2 Me Br
-398 Cl SEt Br-398 Cl SEt Br
-399 Cl SOEt Br-399 Cl SOEt Br
-400 Cl S02Et Br-400 Cl S0 2 Et Br
-401 Cl Me SMe-401 Cl Me SMe
-402 Cl Me S02Me-402 Cl Me S0 2 Me
-403 Cl Me S02Et-403 Cl Me S0 2 Et
-404 Cl C02H S02Me-404 Cl C0 2 H S0 2 Me
-405 Cl COOMe S02Me-405 Cl COOMe Me 2 S0
-406 Cl CONMe2 S02Me Nr. X Y Z Physikalische Daten -406 Cl CONMe 2 S0 2 Me No. XYZ Physical Data
( H-NMR, DMSO-d6, 400 MHz)-407 Cl CONMe(OMe) S02Me(H-NMR, DMSO-d 6 , 400 MHz) -407 Cl CONMe (OMe) SO 2 Me
-408 Cl CH2N(OMe)Et S02Me-408 Cl CH 2 N (OMe) Et SO 2 Me
-409 Cl CH2OMe S02Me-409 Cl CH 2 OMe S0 2 Me
-410 Cl CH2OMe S02Et-410 Cl CH 2 OMe S0 2 Et
-411 Cl CH2OEt S02Me-411 Cl CH 2 OEt S0 2 Me
-412 Cl CH2OEt S02Et-412 Cl CH 2 OEt S0 2 Et
-413 Cl CH2OiPr S02Me-413 Cl CH 2 OiPr S0 2 Me
-414 Cl CH2OcPentyl S02Me-414 Cl CH 2 OcPentyl S0 2 Me
-415 Cl CH2OCH2CHF2 S02Me-415 Cl CH 2 OCH 2 CHF 2 S0 2 Me
-416 Cl CH2OCH2CF3 SMe 9.74 (bs,1 H), 7.70 (d, 1 H), 7.27 -416 Cl CH 2 OCH 2 CF 3 SMe 9.74 (bs, 1 H), 7.70 (d, 1 H), 7.27
(d, 1 H), 4.99 (s,2H), 4.61 (t,2H), 4.27 (q,2H), 3.72 (t,2H), 3.29 (s,3H), 3.22 (s,3H) (d, 1H), 4.99 (s, 2H), 4.61 (t, 2H), 4.27 (q, 2H), 3.72 (t, 2H), 3.29 (s, 3H), 3.22 (s, 3H)
-417 Cl CH2OCH2CF3 S02Me 7.99 (d,1 H), 7.75 (d, 1 H), 5.24 -417 Cl CH 2 OCH 2 CF 3 S0 2 Me 7.99 (d, 1 H), 7.75 (d, 1 H), 5.24
(s,2H), 4.37 (t,2H), 3.92 (q,2H), 3.81 (t,2H), 3.35 (s,3H), 2.55 (s,3H) (s, 2H), 4.37 (t, 2H), 3.92 (q, 2H), 3.81 (t, 2H), 3.35 (s, 3H), 2.55 (s, 3H)
-418 Cl CH2OCH2CF3 S02Et-418 Cl CH 2 OCH 2 CF 3 SO 2 Et
-419 Cl CH2OCH2CF2CHF2 S02Me-419 Cl CH 2 OCH 2 CF 2 CHF 2 S0 2 Me
-420 Cl CH20(CH2)2OMe S02Me-420 Cl CH 2 0 (CH 2 ) 2 OMe S0 2 Me
-421 Cl CH2P03Me2 S02Me-421 Cl CH 2 P0 3 Me 2 S0 2 Me
-422 Cl CH20-tetrahydro-furan-3- S02Me -422 Cl CH 2 O-tetrahydrofuran-3-SO 2 Me
yi yi
-423 Cl CH20-tetrahyd rof u ran-3-yl S02Et-423 Cl CH 2 O-tetrahydrofuran-3-yl SO 2 Et
-424 Cl CH2OCH2- S02Me 9.65 (bs,1 H), 8.18 (d, 1 H), 7.77 tetrahydrofuran-2-yl (d, 1 H), 5.20 (s,2H), 4.61 (t,2H), -424 Cl CH 2 OCH 2 -SO 2 Me 9.65 (bs, 1H), 8.18 (d, 1H), 7.77% tetrahydrofuran-2-yl (d, 1H), 5.20 (s, 2H), 4.61 (t , 2H),
4.08 (m,1 H), 3.83 (t,2H), 3.82- 3.58 (m,4H), 3.37 (s,3H), 3.33 (s,3H), 2.0-1.8 (m,3H), 1.63-1.5 (m, 1 H), 4.08 (m, 1H), 3.83 (t, 2H), 3.82- 3.58 (m, 4H), 3.37 (s, 3H), 3.33 (s, 3H), 2.0-1.8 (m, 3H), 1.63-1.5 (m, 1H),
-425 Cl CH2OCH2- S02Et -425 Cl CH 2 OCH 2 -SO 2 Et
tetrahydrofuran-2-yl tetrahydrofuran-2-yl
-426 Cl CH2OCH2- S02Me -426 Cl CH 2 OCH 2 -SO 2 Me
tetrahydrofuran-3-yl tetrahydrofuran-3-yl
-427 Cl CH2OCH2- S02Et -427 Cl CH 2 OCH 2 -SO 2 Et
tetrahydrofuran-3-yl tetrahydrofuran-3-yl
-428 Cl 4,5-dihydro-1 ,2-oxazol-3 y SMe-428 Cl 4,5-dihydro-1,2-oxazol-3 y SMe
-429 Cl 4,5-dihydro-1 ,2-oxazol-3 S02Me -429 Cl 4,5-dihydro-1,2-oxazole-3 S0 2 Me
yi yi
-430 Cl 4,5-dihydro-1 ,2-oxazol-3 S02Et -430 Cl 4,5-dihydro-1,2-oxazole-3SO 2 Et
yi yi
-431 Cl 5-cyanomethyl- 4,5- S02Me -431 Cl 5-cyanomethyl-4,5-SO 2 Me
dihydro-1 ,2-oxazol-3 yl dihydro-1,2-oxazol-3-yl
-432 Cl 5-cyanomethyl- 4,5- S02Et 10.35 (bs,1 H), 8.14 (d, 1 H), 7.93 dihydro-1 ,2-oxazol-3 yl (d, 1 H), 5.16 (m,1 H), 4.65 (t,2H), -432 Cl 5-cyanomethyl-4,5-S0 2 Et 10.35 (bs, 1H), 8.14 (d, 1H), 7.93 dihydro-1,2-oxazol-3-yl (d, 1H), 5.16 ( m, 1H), 4.65 (t, 2H),
3.84 (t,2H), 3.73 (dd,1 H), 3.38 (s,3H), 3.37 (q,2H), 3.27 Nr. X Y Z Physikalische Daten 3.84 (t, 2H), 3.73 (dd, 1H), 3.38 (s, 3H), 3.37 (q, 2H), 3.27 No. XYZ Physical Data
( H-NMR, DMSO-d6, 400 MHz)(H-NMR, DMSO-d 6 , 400 MHz)
(dd,1 H), 2.95 (dd, 1 H), 2.85 (dd,1 H), 1.31 (t,3H)(dd, 1H), 2.95 (dd, 1H), 2.85 (dd, 1H), 1.31 (t, 3H)
-433 Cl 5-(MeOCH2)-4,5-dihydro- S02Me -433 Cl 5- (MeOCH 2 ) -4,5-dihydro- SO 2 Me
1 ,2-oxazol-3 yl 1, 2-oxazol-3 yl
-434 Cl 5-(MeOCH2)-4,5-dihydro- S02Et -434 Cl 5- (MeOCH 2 ) -4,5-dihydro-S0 2 Et
1 ,2-oxazol-3 yl 1, 2-oxazol-3 yl
-435 Cl 5-Me-5-(MeOCH2)-4,5- S02Me -435 Cl 5-Me-5- (MeOCH 2 ) -4.5 S0 2 Me
dihydro-1 ,2-oxazol-3 yl dihydro-1,2-oxazol-3-yl
-436 Cl 5-Me-5-(MeOCH2)-4,5- S02Et -436 Cl 5-Me-5- (MeOCH 2 ) -4.5 S0 2 Et
dihydro-1 ,2-oxazol-3 yl dihydro-1,2-oxazol-3-yl
-437 Cl NH2 S02Me-437 Cl NH 2 S0 2 Me
-438 Cl NHMe S02Me-438 Cl NHMe S0 2 Me
-439 Cl NMe2 S02Me-439 Cl NMe 2 S0 2 Me
-440 Cl NH(CH2)2OMe S02Me-440 Cl NH (CH 2 ) 2 OMe S0 2 Me
-441 Cl NH(CH2)2OMe S02Et-441 Cl NH (CH 2 ) 2 OMe S0 2 Et
-442 Cl NH(CH2)2OEt S02Me-442 Cl NH (CH 2 ) 2 OEt S0 2 Me
-443 Cl NH(CH2)3OMe S02Me-443 Cl NH (CH 2 ) 3 OMe S0 2 Me
-444 Cl NH(CH2)3OMe S02Et-444 Cl NH (CH 2 ) 3 OMe S0 2 Et
-445 Cl NH(CH2)4OMe S02Me-445 Cl NH (CH 2 ) 4 OMe S0 2 Me
-446 Cl NH(CH2)4OMe S02Et-446 Cl NH (CH 2 ) 4 OMe S0 2 Et
-447 Cl pyrazol-1-yl S02Me-447 Cl pyrazol-1-yl SO 2 Me
-448 Cl OMe S02Me-448 Cl OMe S0 2 Me
-449 Cl OMe S02Et-449 Cl OMe S0 2 Et
-450 Cl OEt S02Me 9.41 (bs,1 H), 8.02 (d,1 H), 7.56 -450 Cl OEt S0 2 Me 9.41 (bs, 1 H), 8.02 (d, 1 H), 7.56
(bd,1 H), 4.61 (t,2H), 4.32 (q,2H), 3.84 (t,2H), 3.39 (s,3H), 3.29 (s,3H), 1.42 (t,3H)-451 Cl OEt S02Et(bd, 1H), 4.61 (t, 2H), 4.32 (q, 2H), 3.84 (t, 2H), 3.39 (s, 3H), 3.29 (s, 3H), 1.42 (t, 3H) -451 Cl OEt S0 2 Et
-452 Cl OPr S02Me 9.56 (bs,1 H), 8.02 (d,1 H), 7.55 -452 Cl OPr S0 2 Me 9.56 (bs, 1H), 8.02 (d, 1H), 7.55
(bd,1 H), 4.62 (t,2H), 4.22 (t,2H), 3.84 (t,2H), 3.39 (s,3H), 3.28 (s,3H), 1.95 (quin,2H), 1.09 (t,3H) (bd, 1H), 4.62 (t, 2H), 4.22 (t, 2H), 3.84 (t, 2H), 3.39 (s, 3H), 3.28 (s, 3H), 1.95 (quin, 2H), 1.09 (t, 3H)
-453 Cl OPr S02Et 11.86 (bs,1 H), 7.93 (d,1 H), 7.71 -453 Cl OPr S0 2 Et 11.86 (bs, 1H), 7.93 (d, 1H), 7.71
(d,1 H), 4.58 (t,2H), 4.15 (t,2H), 3.78 (t,2H), 3.51 (q,2H), 3.24 (s,3H), 1.88 (sex,2H), 1.13 (t,3H), 1.05 (t,3H) (d, 1H), 4.58 (t, 2H), 4.15 (t, 2H), 3.78 (t, 2H), 3.51 (q, 2H), 3.24 (s, 3H), 1.88 (sex, 2H), 1.13 (t, 3H), 1.05 (t, 3H)
-454 Cl OiPr S02Me-454 Cl OiPr S0 2 Me
-455 Cl OiPr S02Et-455 Cl OiPr S0 2 Et
-456 Cl OAIIyl S02Me 9.35 (bs,1 H), 8.03 (d,1 H), 7.58 -456 Cl OAIIyl S0 2 Me 9.35 (bs, 1H), 8.03 (d, 1H), 7.58
(bd,1 H), 6.19 (m,1 H), 5.51 (dd,1 H), 5.37 (dd,1 H), 4.75 (d,2H), 4.61 (t,2H), 3.84 (t,2H), 3.40 (s,3H), 3.28 (s,3H)-457 Cl OAIIyl S02Et Nr. X Y Z Physikalische Daten (bd, 1H), 6.19 (m, 1H), 5.51 (dd, 1H), 5.37 (dd, 1H), 4.75 (d, 2H), 4.61 (t, 2H), 3.84 (t, 2H ), 3.40 (s, 3H), 3.28 (s, 3H) -457 Cl OAIIyl S0 2 Et No. XYZ Physical Data
( H-NMR, DMSO-d6,400 MHz)-458 Cl OPropargyl S02Me 9.63 (bs,1H), 8.03 (d,1H), 7.61 (H-NMR, DMSO-d 6 , 400 MHz) -458 Cl OPropargyl S0 2 Me 9.63 (bs, 1H), 8.03 (d, 1H), 7.61
(bd,1H), 4.92 (s,2H), 4.63 (t,2H), 3.84 (t,2H), 3.40 (s,3H), 3.32 (s,3H), 2.66 (t,1H)-459 Cl OPropargyl S02Et(bd, 1H), 4.92 (s, 2H), 4.63 (t, 2H), 3.84 (t, 2H), 3.40 (s, 3H), 3.32 (s, 3H), 2.66 (t, 1H) -459 Cl OPropargyl S0 2 Et
-460 Cl 0(CH2)2F S02Me 9.50 (bs,1H), 8.04 (d,1H), 7.52 -460 Cl 0 (CH 2 ) 2 F S0 2 Me 9.50 (bs, 1H), 8.04 (d, 1H), 7.52
(bd,1H), 3.89-3.91 (m,1H), 4.77-4.79 (m,1H), 4.62 (t,2H), 4.55 (bs,1H), 4.48 (bs,1H), 3.84 (t,2H), 3.40 (s,3H), 3.31 (s,3H)-461 Cl 0(CH2)2F S02Et(bd, 1H), 3.89-3.91 (m, 1H), 4.77-4.79 (m, 1H), 4.62 (t, 2H), 4.55 (bs, 1H), 4.48 (bs, 1H), 3.84 (t, 2H ), 3.40 (s, 3H), 3.31 (s, 3H) -461 Cl 0 (CH 2 ) 2 F S0 2 Et
-462 Cl 0(CH2)2CI S02Me 9.56 (bs,1H), 8.04 (d,1H), 7.52 -462 Cl 0 (CH 2 ) 2 CI S0 2 Me 9.56 (bs, 1H), 8.04 (d, 1H), 7.52
(bd,1H), 4.62 (t,2H), 4.51 (t,2H), 3.95 (t,2H), 3.84 (t,2H), 3.41 (s,3H), 3.32 (s,3H) (bd, 1H), 4.62 (t, 2H), 4.51 (t, 2H), 3.95 (t, 2H), 3.84 (t, 2H), 3.41 (s, 3H), 3.32 (s, 3H)
-463 Cl 0(CH2)2CI S02Et 9.61 (bs,1H), 8.02 (d,1H), 7.60 -463 Cl 0 (CH 2 ) 2 Cl S0 2 Et 9.61 (bs, 1H), 8.02 (d, 1H), 7.60
(bd,1H), 4.62 (t,2H), 4.50 (t,2H), 3.94 (t,2H), 3.84 (t,2H), 3.48 (q,2H), 3.40 (s,3H), 1.28 (t,3H)-464 Cl OCH2cPr S02Me 9.42 (bs,1H), 8.02 (d,1H), 7.55 (bd, 1H), 4.62 (t, 2H), 4.50 (t, 2H), 3.94 (t, 2H), 3.84 (t, 2H), 3.48 (q, 2H), 3.40 (s, 3H), 1.28 ( t, 3H) -464 Cl OCH 2 cPr S0 2 Me 9.42 (bs, 1H), 8.02 (d, 1H), 7.55
(d,1H), 4.61 (t,2H), 4.09 (d,2H), 3.83 (t,2H), 3.39 (s,3H), 3.33 (s,3H), 1.40-1.49 (m,1H), 0.65- 0.70 (m,2H), 0.45-0.50 (m,2H)-465 Cl OCH2cPr S02Et 9.50 (bs,1H), 8.00 (d,1H), 7.56 (d, 1H), 4.61 (t, 2H), 4.09 (d, 2H), 3.83 (t, 2H), 3.39 (s, 3H), 3.33 (s, 3H), 1.40-1.49 (m, 1H), 0.65-0.70 (m, 2H), 0.45-0.50 (m, 2H) -465 Cl OCH 2 cPr S0 2 Et 9.50 (bs, 1H), 8.00 (d, 1H), 7.56
(d,1H), 4.62 (t,2H), 4.08 (d,2H), 3.84 (t,2H), 3.51 (q,2H), 3.38 (s,3H), 1.42-1.46 (m,1H), 1.27 (t,3H), 0.65-0.70 (m,2H), 0.44- 0.48 (m,2H) (d, 1H), 4.62 (t, 2H), 4.08 (d, 2H), 3.84 (t, 2H), 3.51 (q, 2H), 3.38 (s, 3H), 1.42-1.46 (m, 1H), 1.27 (t, 3H), 0.65-0.70 (m, 2H), 0.44-0.48 (m, 2H)
-466 Cl OCH2cBu S02Me 9.41 (bs,1H), 8.02 (d,1H), 7.55 -466 Cl OCH 2 cBu S0 2 Me 9.41 (bs, 1H), 8.02 (d, 1H), 7.55
(d,1H), 4.62 (t,2H), 4.24 (d,2H), 3.84 (t,2H), 3.39 (s,3H), 3.27 (s,3H), 2.89-2.98 (m,1H), 2.13- 2.21 (m,2H), 1.90-2.05 (m,4H)-467 Cl OCH2cBu S02Et(d, 1H), 4.62 (t, 2H), 4.24 (d, 2H), 3.84 (t, 2H), 3.39 (s, 3H), 3.27 (s, 3H), 2.89-2.98 (m, 1H), 2.13-2.21 (m, 2H), 1.90-2.05 (m, 4H) -467 Cl OCH 2 cBu S0 2 Et
-468 Cl 0(CH2)2OMe S02Me 7.76 (d,1H), 7.47 (d,1H), 4.33 -468 Cl 0 (CH 2 ) 2 OMe SO 2 Me 7.76 (d, 1H), 7.47 (d, 1H), 4.33
(t,2H), 4.27 (t,2H), 3.77 (q,2H), 3.71 (t,2H), 3.36 (s,6H), 3.29 (s,3H) (t, 2H), 4.27 (t, 2H), 3.77 (q, 2H), 3.71 (t, 2H), 3.36 (s, 6H), 3.29 (s, 3H)
-469 Cl 0(CH2)2OMe S02Et-469 Cl 0 (CH2) 2 OMe Et 2 S0
-470 Cl 0(CH2)2OEt S02Me-470 Cl 0 (CH 2 ) 2 OEt S0 2 Me
-471 Cl 0(CH2)3OMe S02Me-471 Cl 0 (CH 2 ) 3 OMe S0 2 Me
-472 Cl 0(CH2)3OMe S02Et-472 Cl 0 (CH 2 ) 3 OMe S0 2 Et
-473 Cl 0(CH2)4OMe S02Me-473 Cl 0 (CH 2 ) 4 OMe S0 2 Me
-474 Cl 0(CH2)4OMe S02Et Nr. X Y Z Physikalische Daten -474 Cl 0 (CH 2 ) 4 OMe S0 2 Et No. XYZ Physical Data
( H-NMR, DMSO-d6,400 MHz)-475 Cl 0(CH2)2OCF3 S02Me 11.88 (bs,1H), 7.97 (d,1H), 7.75 (H-NMR, DMSO-d 6 , 400 MHz) -475 Cl 0 (CH 2 ) 2 OCF 3 SO 2 Me 11.88 (bs, 1H), 7.97 (d, 1H), 7.75
(d,1H), 4.57 (q,2H), 4.54-4.56 (m,2H), 4.43-4.48 (m,2H), 3.78 (t,2H), 3.40 (s,3H), 3.24 (s,3H)-476 Cl 0(CH2)2OCF3 S02Et 11.88 (bs,1H), 7.96 (d,1H), 7.76 (d, 1H), 4.57 (q, 2H), 4.54-4.56 (m, 2H), 4.43-4.48 (m, 2H), 3.78 (t, 2H), 3.40 (s, 3H), 3.24 (s, 3H ) -476 Cl 0 (CH 2 ) 2 OCF 3 SO 2 Et 11.88 (bs, 1H), 7.96 (d, 1H), 7.76
(d,1H), 4.58 (t,2H), 4.53-4.56 (m,2H), 4.43-4.46 (m,2H), 3.78 (t,2H), 3.42 (q,2H), 3.24 (s,3H), 1.15 (t,3H) (d, 1H), 4.58 (t, 2H), 4.53-4.56 (m, 2H), 4.43-4.46 (m, 2H), 3.78 (t, 2H), 3.42 (q, 2H), 3.24 (s, 3H 1.15 (t, 3H)
-477 Cl 0(CH2)2SMe S02Me-477 Cl 0 (CH 2 ) 2 SMe S0 2 Me
-478 Cl 0(CH2)2SEt S02Me-478 Cl 0 (CH 2 ) 2 SEt S0 2 Me
-479 Cl 0(CH2)3SMe S02Me-479 Cl 0 (CH 2 ) 3 SMe S0 2 Me
-480 Cl OCH2-tetrahydrofuran-2-yl S02Me-480 Cl OCH 2 -tetrahydrofuran-2-yl SO 2 Me
-481 Cl OCH2-tetrahydrofuran-2-yl S02Et-481 Cl OCH 2 -tetrahydrofuran-2-yl S0 2 Et
-482 Cl [1 ,4]dioxan-2-yl-methoxy S02Me-482 Cl [1, 4] dioxan-2-ylmethoxy S0 2 Me
-483 Cl [1 ,4]dioxan-2-yl-methoxy S02Et-483 Cl [1,4] dioxan-2-yl-methoxy S0 2 Et
-484 Cl OCH2(CO)NMe2 S02Me 10.6 (brs,1H), 8.02 (d,1H), 7.63 -484 Cl OCH 2 (CO) NMe 2 S0 2 Me 10.6 (brs, 1H), 8.02 (d, 1H), 7.63
(d,1H), 4.94 (s,2H), 4.64 (t,2H), 3.84 (t,2H), 3.44 (s,3H), 3.37 (s,3H), 3.03 (s,3H), 2.93 (s,3H)-485 Cl OCH2(CO)NMe2 S02Et 10.7 (bs,1H), 8.00 (d,1H), 7.63 (d, 1H), 4.94 (s, 2H), 4.64 (t, 2H), 3.84 (t, 2H), 3.44 (s, 3H), 3.37 (s, 3H), 3.03 (s, 3H), 2.93 ( s, 3H) -485 Cl OCH 2 (CO) NMe 2 S0 2 Et 10.7 (bs, 1H), 8.00 (d, 1H), 7.63
(d,1H), 4.93 (s,2H), 4.65 (t,2H), 3.83 (t,2H), 3.64 (q,2H), 3.36 (s,3H), 3.02 (s,3H), 2.94 (s,3H), 1.26 (t,3H) (d, 1H), 4.93 (s, 2H), 4.65 (t, 2H), 3.83 (t, 2H), 3.64 (q, 2H), 3.36 (s, 3H), 3.02 (s, 3H), 2.94 ( s, 3H), 1.26 (t, 3H)
-486 Cl F SMe-486 Cl F SMe
-487 Cl Cl S02Me 9.9 (brs,1H), 8.21 (d,1H), 7.74 -487 Cl Cl S0 2 Me 9.9 (brs, 1H), 8.21 (d, 1H), 7.74
(d,1H), 4.63 (t,2H), 3.84 (t,2H), 3.39 (s,3H), 3.33 (s,3H)-488 Cl SMe S02Me 11.9 (brs,1H), 8.15 (d,1H), 7.94 (d, 1H), 4.63 (t, 2H), 3.84 (t, 2H), 3.39 (s, 3H), 3.33 (s, 3H) -488 Cl SMe S0 2 Me 11.9 (brs, 1H), 8.15 (i.e. , 1H), 7.94
(d,1H), 4.58 (t,2H), 3.78 (t,2H), 3.59 (s,3H), 3.24 (s,3H), 2.50 (s,3H) (d, 1H), 4.58 (t, 2H), 3.78 (t, 2H), 3.59 (s, 3H), 3.24 (s, 3H), 2.50 (s, 3H)
-489 Cl SOMe S02Me 11.8 (brs,1H), 8.05 (d,1H), 7.89 -489 Cl SOMe S0 2 Me 11.8 (brs, 1H), 8.05 (d, 1H), 7.89
(d,1H), 4.42 (t,2H), 3.73 (t,2H), 3.51 (s,3H), 3.22 (s,3H), 3.18 (s,3H), (d, 1H), 4.42 (t, 2H), 3.73 (t, 2H), 3.51 (s, 3H), 3.22 (s, 3H), 3.18 (s, 3H),
-490 Cl S02Me S02Me 12.0 (brs,1H), 8.39 (d,1H), 8.27 -490 Cl S0 2 Me S0 2 Me 12.0 (brs, 1H), 8.39 (d, 1H), 8.27
(d,1H), 4.59 (t,2H), 3.78 (t,2H), 3.67 (s,3H), 3.58 (s,3H), 3.24 (s,3H), (d, 1H), 4.59 (t, 2H), 3.78 (t, 2H), 3.67 (s, 3H), 3.58 (s, 3H), 3.24 (s, 3H),
-491 Br OMe Br 9.80 (brs,1H), 7.65 (d,1H), 7.30 -491 Br OMe Br 9.80 (brs, 1H), 7.65 (d, 1H), 7.30
(d,1H), 4.65 (t,2H), 3.92 (s,3H), 3.84 (t,2H), 3.36 (s,3H)-492 Br 0(CH2)2OMe Br(d, 1H), 4.65 (t, 2H), 3.92 (s, 3H), 3.84 (t, 2H), 3:36 (s, 3H) -492 0 Br (CH 2) 2 OMe Br
-493 Br 0(CH2)3OMe Br Nr. X Y Z Physikalische Daten -493 0 Br (CH 2) 3 OMe Br No. XYZ Physical Data
( H-NMR, DMSO-d6, 400 MHz)-494 Br OMe S02Me 9.60 (brs, 1 H), 7.89 (d,1 H), 7.23 (H-NMR, DMSO-d 6 , 400 MHz) -494 Br OMe S0 2 Me 9.60 (brs, 1H), 7.89 (d, 1H), 7.23
(d, 1 H), 4.66 (t,2H), 4.06 (s,3H), 3.82 (t,2H), 3.41 (s,3H), 3.22 (s,3H) (d, 1H), 4.66 (t, 2H), 4.06 (s, 3H), 3.82 (t, 2H), 3.41 (s, 3H), 3.22 (s, 3H)
-495 Br OMe S02Et-495 Br OMe S0 2 Et
-496 Br OEt S02Me-496 Br OEt S0 2 Me
-497 Br OEt S02Et-497 Br OEt S0 2 Et
-498 Br OPr S02Me-498 Br OPr S0 2 Me
-499 Br OPr S02Et-499 Br OPr S0 2 Et
-500 Br 0(CH2)2OMe S02Me-500 Br 0 (CH 2 ) 2 OMe S0 2 Me
-501 Br 0(CH2)2OMe S02Et-501 Br 0 (CH 2 ) 2 OMe S0 2 Et
-502 Br 0(CH2)3OMe S02Me-502 Br 0 (CH 2 ) 3 OMe S0 2 Me
-503 Br 0(CH2)3OMe S02Et-503 Br 0 (CH 2 ) 3 OMe S0 2 Et
-504 Br 0(CH2)4OMe S02Me-504 Br 0 (CH 2 ) 4 OMe S0 2 Me
-505 Br 0(CH2)4OMe S02Et-505 Br 0 (CH 2 ) 4 OMe S0 2 Et
-506 Br [1 ,4]dioxan-2-yl-methoxy S02Me-506 Br [1,4] dioxan-2-yl-methoxy S0 2 Me
-507 Br [1 ,4]dioxan-2-yl-methoxy S02Et-507 Br [1, 4] dioxan-2-yl-methoxy S0 2 Et
-508 I 0(CH2)2OMe S02Me-508 I 0 (CH 2 ) 2 OMe S0 2 Me
-509 I 0(CH2)2OMe S02Et-509 I 0 (CH 2 ) 2 OMe S0 2 Et
-510 I 0(CH2)3OMe S02Me-510 I 0 (CH 2 ) 3 OMe S0 2 Me
-511 I 0(CH2)3OMe S02Et-511 I 0 (CH 2 ) 3 OMe S0 2 Et
-512 I 0(CH2)4OMe S02Me-512 I 0 (CH 2 ) 4 OMe S0 2 Me
-513 I 0(CH2)4OMe S02Et-513 I 0 (CH 2 ) 4 OMe S0 2 Et
-514 I [1 ,4]dioxan-2-yl-methoxy S02Me-514 I [1,4] dioxan-2-yl-methoxy S0 2 Me
-515 I [1 ,4]dioxan-2-yl-methoxy S02Et-515 I [1,4] dioxan-2-yl-methoxy S0 2 Et
-516 OH S02Me CF3 -516 OH S0 2 Me CF 3
-517 OMe SMe CF3 7.76 (d,H), 7.68 (d, 1 H), 4.53 -517 OMe SMe CF 3 7.76 (d, H), 7.68 (d, 1 H), 4.53
(t,2H), 3.96 (s,3H), 3.77 (t,2H), 3.24 (s,3H), 2.44 (s,3H)-518 OMe SOMe CF3 7.76 (d,1 H), 7.68 (d, 1 H), 4.53 (t, 2H), 3.96 (s, 3H), 3.77 (t, 2H), 3.24 (s, 3H), 2.44 (s, 3H) -518 OMe SOMe CF 3 7.76 (d, 1H), 7.68 (i.e. , 1 H), 4.53
(t,2H), 3.96 (s,3H), 3.77 (t,2H), 3.24 (s,3H), 2.44 (s,3H)-519 OMe S02Me CF3 (t, 2H), 3.96 (s, 3H), 3.77 (t, 2H), 3.24 (s, 3H), 2.44 (s, 3H) -519 OMe S0 2 Me CF 3
-520 OMe SEt CF3 -520 OMe SEt CF 3
-521 OMe SOEt CF3 -521 OMe SOEt CF 3
-522 OMe S02Et CF3 -522 OMe S0 2 Et CF 3
-523 OMe S(CH2)2OMe CF3 -523 OMe S (CH 2 ) 2 OMe CF 3
-524 OMe SO(CH2)2OMe CF3 -524 OMe SO (CH 2 ) 2 OMe CF 3
-525 OMe S02(CH2)2OMe CF3 -525 OMe S0 2 (CH 2 ) 2 OMe CF 3
-526 OMe CH2N(S02Me)Et Cl Nr. X Y Z Physikalische Daten -526 OMe CH 2 N (S0 2 Me) Et Cl No. XYZ Physical Data
( H-NMR, DMSO-d6, 400 MHz)-527 OMe NHCOMe Cl 10.26 (bs,1 H), 7.99 (d, 1 H), 7.38 (H-NMR, DMSO-d 6 , 400 MHz) -527 OMe NHCOMe Cl 10.26 (bs, 1H), 7.99 (d, 1H), 7.38
(d, 1 H), 4.57 (t,2H), 3.95 (s,3H), 3.80 (t,2H), 3.30 (s,3H), 2.30 (bs,3H) (d, 1H), 4.57 (t, 2H), 3.95 (s, 3H), 3.80 (t, 2H), 3.30 (s, 3H), 2.30 (bs, 3H)
-528 OMe NHCOEt Cl-528 OMe NHCOEt Cl
-529 OMe NHCOiPr Cl-529 OMe NHCOiPr Cl
-530 OMe NHCOcycPr Cl-530 OMe NHCOcycPr Cl
-531 OMe NHCOCHCMe2 Cl-531 OMe NHCOCHCMe 2 Cl
-532 OMe NHCOPh Cl-532 OMe NHCOPh Cl
-533 OMe SMe Cl-533 OMe SMe Cl
-534 OMe SOMe Cl-534 OMe SOMe Cl
-535 OMe S02Me Cl-535 OMe S0 2 Me Cl
-536 OMe SEt Cl-536 OMe SEt Cl
-537 OMe SOEt Cl-537 OMe SOEt Cl
-538 OMe S02Et Cl-538 OMe S0 2 Et Cl
-539 OMe S(CH2)2OMe Cl-539 OMe S (CH 2 ) 2 OMe Cl
-540 OMe SO(CH2)2OMe Cl-540 OMe SO (CH 2 ) 2 OMe Cl
-541 OMe S02(CH2)2OMe Cl-541 OMe S0 2 (CH 2 ) 2 OMe Cl
-542 OEt SMe Cl-542 OEt SMe Cl
-543 OEt SOMe Cl-543 OEt SOMe Cl
-544 OEt S02Me Cl-544 OEt S0 2 Me Cl
-545 OCH2c-Pr SMe CF3 -545 OCH 2 c-Pr SMe CF 3
-546 OCH2c-Pr SOMe CF3 -546 OCH 2 c-Pr SOMe CF 3
-547 OCH2c-Pr S02Me CF3 -547 OCH 2 c-Pr S0 2 Me CF 3
-548 OCH2c-Pr SEt CF3 -548 OCH 2 c-Pr SEt CF 3
-549 OCH2c-Pr SOEt CF3 -549 OCH 2 c-Pr SOEt CF 3
-550 OCH2c-Pr S02Et CF3 -550 OCH 2 c-Pr S0 2 Et CF 3
-551 OCH2c-Pr S(CH2)2OMe CF3 -551 OCH 2 c-Pr S (CH 2 ) 2 OMe CF 3
-552 OCH2c-Pr SO(CH2)2OMe CF3 -552 OCH 2 c-Pr SO (CH 2 ) 2 OMe CF 3
-553 OCH2c-Pr S02(CH2)2OMe CF3 -553 OCH 2 c-Pr S0 2 (CH 2 ) 2 OMe CF 3
-554 OCH2c-Pr SMe Cl-554 OCH 2 c-Pr SMe Cl
-555 OCH2c-Pr SOMe Cl-555 OCH 2 c-Pr SOMe Cl
-556 OCH2c-Pr S02Me Cl-556 OCH 2 c-Pr S0 2 Me Cl
-557 OCH2c-Pr SEt Cl-557 OCH 2 c-Pr SEt Cl
-558 OCH2c-Pr SOEt Cl-558 OCH 2 c-Pr SOEt Cl
-559 OCH2c-Pr S02Et Cl-559 OCH 2 c-Pr S0 2 Et Cl
-560 OCH2c-Pr S(CH2)2OMe Cl-560 OCH 2 c-Pr S (CH 2 ) 2 OMe Cl
-561 OCH2c-Pr SO(CH2)2OMe Cl-561 OCH 2 c-Pr SO (CH 2 ) 2 OMe Cl
-562 OCH2c-Pr S02(CH2)2OMe Cl-562 OCH 2 c-Pr S0 2 (CH 2 ) 2 OMe Cl
-563 OCH2c-Pr SMe S02Me-563 OCH 2 c-Pr SMe S0 2 Me
-564 OCH2c-Pr SOMe S02Me Nr. X Y Z Physikalische Daten -564 OCH 2 c-Pr SOMe S0 2 Me No. XYZ Physical Data
( H-NMR, DMSO-d6,400 MHz)-565 OCH2c-Pr S02Me S02Me(H-NMR, DMSO-d 6 , 400 MHz) -565 OCH 2 c-Pr S0 2 Me S0 2 Me
-566 OCH2c-Pr SEt S02Me-566 OCH 2 c-Pr SEt S0 2 Me
-567 OCH2c-Pr SOEt S02Me-567 OCH 2 c-Pr SOEt S0 2 Me
-568 OCH2c-Pr S02Et S02Me-568 OCH 2 c-Pr S0 2 Et S0 2 Me
-569 OCH2c-Pr S(CH2)2OMe S02Me-569 OCH 2 c-Pr S (CH 2 ) 2 OMe S0 2 Me
-570 OCH2c-Pr SO(CH2)2OMe S02Me-570 OCH 2 c-Pr SO (CH 2 ) 2 OMe S0 2 Me
-571 OCH2c-Pr S02(CH2)2OMe S02Me-571 OCH 2 c-Pr S0 2 (CH 2 ) 2 OMe S0 2 Me
-572 OS02Me SMe CF3 11.87 (brs,1H), 7.98 (d,H), 7.94 -572 OS0 2 Me SMe CF 3 11.87 (brs, 1H), 7.98 (d, H), 7.94
(d,1H), 4.57 (t,2H), 3.78 (t,2H), 3.61 (s,3H), 3.24 (s,3H), 2.52 (s,3H) (d, 1H), 4.57 (t, 2H), 3.78 (t, 2H), 3.61 (s, 3H), 3.24 (s, 3H), 2.52 (s, 3H)
-573 OS02Me SOMe CF3 -573 OS0 2 Me SOMe CF 3
-574 OS02Me S02Me CF3 -574 OS0 2 Me S0 2 Me CF 3
-575 SMe SMe H-575 SMe SMe H
-576 S02Me S02Me H-576 S0 2 Me S0 2 Me H
-577 SMe SMe F-577 SMe SMe F
-578 SMe SEt F-578 SMe SEt F
-579 S02Me NHEt Cl-579 S0 2 Me NHEt Cl
-580 SMe OCH2CHF2 Br-580 SMe OCH 2 CHF 2 Br
-581 S02Me F CF3 -581 S0 2 Me F CF 3
-582 S02Me NH2 CF3 -582 S0 2 Me NH 2 CF 3
-583 Cl SMe CF3 11.9 (brs,1H), 7.98 (d,1H), 7.93 -583 Cl SMe CF 3 11.9 (brs, 1H), 7.98 (d, 1H), 7.93
(d,1H), 4.59 (t,2H), 3.78 (t,2H), 3.24 (s,3H), 2.45 (s,3H)-584 Cl SOMe CF3 11.9 (brs,1H), 8.07 (s,2H), 4.59 (d, 1H), 4.59 (t, 2H), 3.78 (t, 2H), 3.24 (s, 3H), 2.45 (s, 3H) -584 Cl SOMe CF 3 11.9 (brs, 1H), 8.07 (s, 2H), 4.59
(t,2H), 3.78 (t,2H), 3.24 (s,3H), 3.16 (s,3H) (t, 2H), 3.78 (t, 2H), 3.24 (s, 3H), 3.16 (s, 3H)
-585 Cl S02Me CF3 12.0 (brs,1H), 8.21 (2d, 2H), -585 Cl S0 2 Me CF 3 12.0 (brs, 1H), 8.21 (2d, 2H),
4.59 (t,2H), 3.78 (t,2H), 3.54 (s,3H), 3.24 (s,3H) 4.59 (t, 2H), 3.78 (t, 2H), 3.54 (s, 3H), 3.24 (s, 3H)
-586 Cl OCHF2 S02Me 10.95 (bs,1H), 8.11 (d,1H) 7.74 -586 Cl OCHF 2 S0 2 Me 10.95 (bs, 1H), 8.11 (d, 1H) 7.74
(bd,1H), 6.84 (t,1H), 4.64 (t,2H), 3.84 (t,2H), 3.40 (s,3H), 3.28 (s,3H) (bd, 1H), 6.84 (t, 1H), 4.64 (t, 2H), 3.84 (t, 2H), 3.40 (s, 3H), 3.28 (s, 3H)
-587 Cl OCHF2 S02Et 10.05 (bs,1H), 8.09 (d,1H), 7.75 -587 Cl OCHF 2 S0 2 Et 10.05 (bs, 1H), 8.09 (d, 1H), 7.75
(bd,1H), 6.86 (t,1H), 4.64 (t,2H), 3.84 (t,2H), 3.40 (q,2H), 3.40 (s,3H), 1.30 (t,3H) (bd, 1H), 6.86 (t, 1H), 4.64 (t, 2H), 3.84 (t, 2H), 3.40 (q, 2H), 3.40 (s, 3H), 1.30 (t, 3H)
-588 Me 0(CH2)2SOEt Br 9.41 (bs,1H), 7.53 (d,1H), 7.23 -588 Me 0 (CH 2 ) 2 SOEt Br 9.41 (bs, 1H), 7.53 (d, 1H), 7.23
(d,1H), 4.60 (t,2H), 4.31-4.42 (m,2H), 3.83 (t,2H), 3.37 (s,3H), 3.23-3.30 (m,1H), 3.02-3.09 (m,1H), 2.83-2.94 (m,2H), 2.54 (s,3H), 1.42 (t,3H) Nr. X Y Z Physikalische Daten (d, 1H), 4.60 (t, 2H), 4.31-4.42 (m, 2H), 3.83 (t, 2H), 3.37 (s, 3H), 3.23-3.30 (m, 1H), 3.02-3.09 (m , 1H), 2.83-2.94 (m, 2H), 2.54 (s, 3H), 1.42 (t, 3H) No. XYZ Physical Data
( H-NMR, DMSO-d6, 400 MHz)-589 Me 0(CH2)2S02Et Br 9.58 (bs, 1 H), 7.55 (d, 1 H), 7.24 (H-NMR, DMSO-d 6 , 400 MHz) -589 Me 0 (CH 2 ) 2 S0 2 Et Br 9.58 (bs, 1H), 7.55 (d, 1H), 7.24
(d, 1 H), 4.62 (t,2H), 4.35 (t,2H), 3.83 (t,2H), 3.50 (t,2H), 3.37 (s,3H), 3.29 (q,2H), 2.53 (s,3H), 1.48 (t,3H) (d, 1H), 4.62 (t, 2H), 4.35 (t, 2H), 3.83 (t, 2H), 3.50 (t, 2H), 3.37 (s, 3H), 3.29 (q, 2H), 2.53 (s, 3H), 1.48 (t, 3H)
-590 Cl 0(CH2)2SMe Cl 9.71 (bs, 1 H), 7.47 (s,2H), 4.61 -590 Cl 0 (CH 2 ) 2 SMe Cl 9.71 (bs, 1H), 7.47 (s, 2H), 4.61
(t,2H), 4.21 (t,2H), 3.82 (t,2H), 3.36 (s,3H), 2.98 (t,2H), 2.22 (s,3H) (t, 2H), 4.21 (t, 2H), 3.82 (t, 2H), 3.36 (s, 3H), 2.98 (t, 2H), 2.22 (s, 3H)
-591 Et SEt CF3 7.70 (d,1 H), 7.57 (d, 1 H), 4.63 -591 Et SEt CF 3 7.70 (d, 1H), 7.57 (d, 1H), 4.63
(t,2H), 3.83 (t,2H), 3.34 (s,3H), 3.27 (q,2H), 2.80 (q,2H), 1.29 - 1.23 (m,6H) (t, 2H), 3.83 (t, 2H), 3.34 (s, 3H), 3.27 (q, 2H), 2.80 (q, 2H), 1.29 - 1.23 (m, 6H)
-592 Et SOEt CF3 7.74 - 7.62 (m,2H), 4.62 (t,2H), -592 Et SOEt CF 3 7.74 - 7.62 (m, 2H), 4.62 (t, 2H),
3.83 (t,2H), 3.63 (m,1 H), 3.52 - 3.25 (m,2H), 3.35 (s,3H), 2.95 (m, 1 H), 1.46 (t,3H), 1.29 (t,3H)-593 Et S02Et CF3 7.91 (d,1 H), 7.76 (m,1 H), 4.61 3.83 (t, 2H), 3.63 (m, 1H), 3.52 - 3.25 (m, 2H), 3.35 (s, 3H), 2.95 (m, 1H), 1.46 (t, 3H), 1.29 (t, 3H) -593 Et S0 2 Et CF 3 7.91 (d, 1H), 7.76 (m, 1H), 4.61
(t,2H), 3.83 (t,2H), 3.50 - 3.13 (m,7H), 1.50 (t,3H), 1.34 (t,3H)-594 cPr SOMe CF3 (t, 2H), 3.83 (t, 2H), 3.50-3.13 (m, 7H), 1.50 (t, 3H), 1.34 (t, 3H) -594 cPr SOMe CF 3
-595 Et SEt Cl-595 Et SEt Cl
-596 Et SOEt Cl-596 Et SOEt Cl
-597 Et S02Et Cl-597 Et S0 2 Et Cl
-598 OMe SMe CHF2 8.21 (d,1 H), 7.64 (d, 1 H), 7.23 -598 OMe SMe CHF 2 8.21 (d, 1 H), 7.64 (d, 1 H), 7.23
(t, 1 H), 4.60 (t,2H), 4.12 (s,3H), 3.82 (t,2H), 3.35 (s,3H), 2.46 (s,3H) in CDCI3 (t, 1H), 4.60 (t, 2H), 4.12 (s, 3H), 3.82 (t, 2H), 3.35 (s, 3H), 2.46 (s, 3H) in CDCl 3
-599 OMe SOMe CHF2 -599 OMe SOMe CHF 2
-600 OMe S02Me CHF2 -600 OMe S0 2 Me CHF 2
-601 OMe SEt CHF2 -601 OMe SEt CHF 2
-602 OMe SOEt CHF2 -602 OMe SOEt CHF 2
-603 OMe S02Et CHF2 -603 OMe S0 2 Et CHF 2
-604 OMe S(CH2)2OMe CHF2 -604 OMe S (CH 2 ) 2 OMe CHF 2
-605 OMe SO(CH2)2OMe CHF2 -605 OMe SO (CH 2 ) 2 OMe CHF 2
-606 OMe S02(CH2)2OMe CHF2 -606 OMe S0 2 (CH 2 ) 2 OMe CHF 2
-607 CH2OMe SMe Cl-607 CH 2 OMe SMe Cl
-608 CH2OMe SOMe Cl-608 CH 2 OMe SOMe Cl
-609 CH2OMe S02Me Cl-609 CH 2 OMe S0 2 Me Cl
-610 CH2OMe SEt Cl-610 CH 2 OMe SEt Cl
-611 CH2OMe SOEt Cl-611 CH 2 OMe SOEt Cl
-612 CH2OMe S02Et Cl-612 CH 2 OMe S0 2 Et Cl
-613 CH2OMe S(CH2)2OMe Cl-613 CH 2 OMe S (CH 2 ) 2 OMe Cl
-614 CH2OMe SO(CH2)2OMe Cl-614 CH 2 OMe SO (CH 2 ) 2 OMe Cl
-615 CH2OMe S02(CH2)2OMe Cl Nr. X Y Z Physikalische Daten -615 CH 2 OMe S0 2 (CH 2 ) 2 OMe Cl No. XYZ Physical Data
( H-NMR, DMSO-d6, 400 MHz)-616 CH2OMe SMe CF3 (H-NMR, DMSO-d 6 , 400 MHz) -616 CH 2 OMe SMe CF 3
-617 CH2OMe SOMe CF3 -617 CH 2 OMe SOMe CF 3
-618 CH2OMe S02Me CF3 -618 CH 2 OMe S0 2 Me CF 3
-619 CH2OMe SEt CF3 -619 CH 2 OMe SEt CF 3
-620 CH2OMe SOEt CF3 -620 CH 2 OMe SOEt CF 3
-621 CH2OMe S02Et CF3 -621 CH 2 OMe S0 2 Et CF 3
-622 CH2OMe S(CH2)2OMe CF3 -622 CH 2 OMe S (CH 2 ) 2 OMe CF 3
-623 CH2OMe SO(CH2)2OMe CF3 -623 CH 2 OMe SO (CH 2 ) 2 OMe CF 3
-624 CH2OMe S02(CH2)2OMe CF3 -624 CH 2 OMe S0 2 (CH 2 ) 2 OMe CF 3
-625 CH2OMe SMe S02Me-625 CH 2 OMe SMe S0 2 Me
-626 CH2OMe SOMe S02Me-626 CH 2 OMe SOMe S0 2 Me
-627 CH2OMe S02Me S02Me-627 CH 2 OMe S0 2 Me S0 2 Me
-628 CH2OMe SEt S02Me-628 CH 2 OMe SEt S0 2 Me
-629 CH2OMe SOEt S02Me-629 CH 2 OMe SOEt S0 2 Me
-630 CH2OMe S02Et S02Me-630 CH 2 OMe S0 2 Et S0 2 Me
-631 CH2OMe S(CH2)2OMe S02Me-631 CH 2 OMe S (CH 2 ) 2 OMe S0 2 Me
-632 CH2OMe SO(CH2)2OMe S02Me-632 CH 2 OMe SO (CH 2 ) 2 OMe S0 2 Me
-633 CH2OMe S02(CH2)2OMe S02Me-633 CH 2 OMe S0 2 (CH 2 ) 2 OMe S0 2 Me
-634 Et SEt S02Me-634 Et SEt S0 2 Me
-635 Et SOEt S02Me-635 et SOEt S0 2 Me
-636 Et S02Et S02Me-636 Et S0 2 Et S0 2 Me
-637 Cl S(CH2)2OMe Cl-637 Cl S (CH 2 ) 2 OMe Cl
-638 Cl SO(CH2)2OMe Cl-638 Cl SO (CH 2 ) 2 OMe Cl
-639 Cl S02(CH2)2OMe Cl-639 Cl SO 2 (CH 2 ) 2 OMe Cl
-640 Cl SEt S02Me-640 Cl SEt S0 2 Me
-641 Cl SOEt S02Me-641 Cl SOEt S0 2 Me
-642 Cl S02Et S02Me-642 Cl S0 2 Et S0 2 Me
-643 Cl S(CH2)2OMe S02Me-643 Cl S (CH 2 ) 2 OMe S0 2 Me
-644 Cl SO(CH2)2OMe S02Me-644 Cl SO (CH 2 ) 2 OMe S0 2 Me
-645 Cl S02(CH2)2OMe S02Me-645 Cl S0 2 (CH 2) 2 OMe S0 2 Me
-646 Cl SEt CF3 -646 Cl SEt CF 3
-647 Cl SOEt CF3 -647 Cl SOEt CF 3
-648 Cl S02Et CF3 -648 Cl S0 2 Et CF 3
-649 Cl S(CH2)2OMe CF3 -649 Cl S (CH 2 ) 2 OMe CF 3
-650 Cl SO(CH2)2OMe CF3 -650 Cl SO (CH 2 ) 2 OMe CF 3
-651 Cl S02(CH2)2OMe CF3 Tabelle 2: Erfindungsgemäße Verbindungen der Formel (I), worin A für CY steht -651 Cl S0 2 (CH 2 ) 2 OMe CF 3 Table 2: Compounds of the invention of formula (I) wherein A is CY
Figure imgf000056_0001
Figure imgf000056_0001
Nr. B R X Y Z Physikalische Daten No. B R X Y Z Physical data
( H-NMR, DMSO-d6,400 MHz) -1 N (CH2)2OH Me S02Me CF3 7.81 (d,H), 7.72 (d,1H), 4.35 (H-NMR, DMSO-d 6 , 400 MHz) -1 N (CH 2 ) 2 OH Me SO 2 Me CF 3 7.81 (d, H), 7.72 (d, 1H), 4.35
(brs,1H), 4.15 (t,2H), 3.72 (t,2H), 3.35 (s,3H), 2.74 (s,3H) -2 N (CH2)2OEt Me S02Me CF3 11.8 (brs,1H), 8.07 (d,H), 8.03 (brs, 1H), 4.15 (t, 2H), 3.72 (t, 2H), 3:35 (s, 3H), 2.74 (s, 3H) -2 N (CH 2) 2 OEt Me Me CF 3 S0 2 11.8 ( brs, 1H), 8.07 (d, H), 8.03
(d,1H), 4.58 (t,2H), 3.79 (t,2H), 3.49 (s,3H), 3.41 (q,2H), 2.76 (s,3H), 1.02 (t,3H) -3 CH (CH2)2OMe Me S02Me CF3 (d, 1H), 4.58 (t, 2H), 3.79 (t, 2H), 3.49 (s, 3H), 3.41 (q, 2H), 2.76 (s, 3H), 1.02 (t, 3H) -3 CH (CH 2 ) 2 OMe Me SO 2 Me CF 3
-4 N (CH2)2OBn Me S02Me CF3 7.90 (d,1H), 7.82 (d,1H), 7.34- 7.21 (m,5H), 4.52 (t,2H), 4.47 (s,2H), 3.83 (t,2H), 3.39 (s,3H), 2.72 (s,3H)-4 N (CH 2) 2 OBn Me S0 2 Me CF 3 7.90 (d, 1H), 7.82 (d, 1H), 7.34- 7.21 (m, 5H), 4:52 (t, 2H), 4:47 (s, 2H ), 3.83 (t, 2H), 3.39 (s, 3H), 2.72 (s, 3H)
-5 N CH2CMe2OMe Me S02Me CF3 11.6 (brs,1H), 7.96 (d,H), 7.84 -5 N CH 2 CMe 2 OMe Me Me CF 3 S0 2 11.6 (brs, 1H), 7.96 (d, H), 7.84
(d,1H), 4.34 (s,2H), 3.40 (s,3H), 3.13 (s,3H), 2.75 (s,3H), 1.13 (s,6H) (d, 1H), 4.34 (s, 2H), 3.40 (s, 3H), 3.13 (s, 3H), 2.75 (s, 3H), 1.13 (s, 6H)
-6 N (CH2)3OMe Me S02Me CF3 7.97(d,1H), 7.92 (d,1H), 4.30 -6N (CH 2 ) 3 OMe Me SO 2 Me CF 3 7.97 (d, 1H), 7.92 (d, 1H), 4.30
(m,2H), 3.39 (s,3H), 3.29 (m,2H), 3.21 (s,3H), 2.76 (s,3H), 2.05 (m,2H) (m, 2H), 3.39 (s, 3H), 3.29 (m, 2H), 3.21 (s, 3H), 2.76 (s, 3H), 2.05 (m, 2H)
-7 N CH2CN Me S02Me CF3 8.15 (d,1H), 8.11 (d,1H), 5.79 -7N CH 2 CN Me S0 2 Me CF 3 8.15 (d, 1H), 8.11 (d, 1H), 5.79
(s,2H), 3.45 (s,3H), 2.75 (s,3H) (s, 2H), 3.45 (s, 3H), 2.75 (s, 3H)
-8 N (CH2)2NMe2 Me S02Me CF3 7.88 (d,1H), 7.82 (d,1H), 4.27 -8N (CH 2 ) 2 NMe 2 Me S0 2 Me CF 3 7.88 (d, 1H), 7.82 (d, 1H), 4.27
(m,2H), 3.71 (m,2H), 3.36 (s,3H), 2.75 (m,2H), 2.15 (s,6H) (m, 2H), 3.71 (m, 2H), 3.36 (s, 3H), 2.75 (m, 2H), 2.15 (s, 6H)
-9 N CH2SiMe3 Me S02Me CF3 7.95-7.89 (m,2H), 3.73 -9N CH 2 SiMe 3 Me SO 2 Me CF 3 7.95-7.89 (m, 2H), 3.73
(s,2H), 3.39 (s,3H), 2.76 (s,3H), 0.13 (s,9H) (s, 2H), 3.39 (s, 3H), 2.76 (s, 3H), 0.13 (s, 9H)
-10 N (CH2)2SiMe3 -10 N (CH 2 ) 2 SiMe 3
-11 N CH2PO(OEt)3 -11N CH 2 PO (OEt) 3
-12 N CH2SMe-12 N CH 2 SMe
-13 N (CH2)2SMe Me S02Me CF3 11.9 (brs,1H), 8.06 (s,2H), -13 N (CH 2 ) 2 SMe Me S0 2 Me CF 3 11.9 (brs, 1H), 8.06 (s, 2H),
4.58 (t,2H), 3.44 (s,3H), 3.02 (t,2H), 2.76 (s,3H), 2.07 (s,3H) -14 N (CH2)2SOMe Me S02Me CF3 8.13 (d,1H), 8.06 (d,1H), 4.85- 4.78 (m,2H), 3.48-3.38 (m,2H), 3.44 (s,3H), 2.77 (s,3H), 2,63 (s,3H) Nr. B R X Y Z Physikalische Daten 4.58 (t, 2H), 3.44 (s, 3H), 3.02 (t, 2H), 2.76 (s, 3H), 2.07 (s, 3H) -14 N (CH 2 ) 2 SOMe Me S0 2 Me CF 3 8.13 (d, 1H), 8.06 (d, 1H), 4.85-4.78 (m, 2H), 3.48-3.38 (m, 2H), 3.44 (s, 3H), 2.77 (s, 3H), 2.63 (s , 3H) No. BRXYZ Physical data
( H-NMR, DMSO-d6,400 MHz) -15 N (CH2)2S02Me Me S02Me CF3 7.98 (brs,2H), 4.73 (t,2H), (H-NMR, DMSO-d 6 , 400 MHz) -15 N (CH 2 ) 2 SO 2 Me Me SO 2 Me CF 3 7.98 (brs, 2H), 4.73 (t, 2H)
3.81 (t,2H), 3.40 (s,3H), 3.05 (s,3H), 2.76 (s,3H) 3.81 (t, 2H), 3.40 (s, 3H), 3.05 (s, 3H), 2.76 (s, 3H)
-16 N (CH2)2CN Me S02Me CF3 -16 N (CH 2) 2 CN Me Me CF 3 S0 2
-17 N (CH2)2N02 Me S02Me CF3 -17N (CH 2 ) 2 NO 2 Me S0 2 Me CF 3
-18 N CH2(2- Me S02Me CF3 -18N CH 2 (2-Me S0 2 Me CF 3
oxopyrrolidin-1- yi) oxopyrrolidin-1-yi)
-19 N CH2CMeOMe Me S02Me CF3 11.71 (brs,1H), 8.07 (d,H), -19 N CH 2 CMeOMe Me S0 2 Me CF 3 11.71 (brs, 1H), 8.07 (d, H),
8.00 (d,1H), 4.54 (dd,1H), 4.40 (dd,1H), 3.78 (m,1H), 3.44 (s,3H), 3.16 (s,3H), 2.76 (s,3H), 1.14 (d,3H)  8.00 (d, 1H), 4.54 (dd, 1H), 4.40 (dd, 1H), 3.78 (m, 1H), 3.44 (s, 3H), 3.16 (s, 3H), 2.76 (s, 3H), 1.14 (d, 3H)
Tabelle 3: Erfindungsgemäße Verbindungen der Formel (I), worin A für N steht Table 3: Compounds according to the invention of the formula (I) in which A is N.
Figure imgf000057_0001
Figure imgf000057_0001
Nr. B R X Z Physikalische Daten No. B R X Z Physical data
( H-NMR, DMSO-d6,400 MHz)-1 CH C2H4OMe Me CF3 (H-NMR, DMSO-d 6 , 400 MHz) -1 CH C 2 H 4 OMe Me CF 3
-2 N C2H4OMe Me CF3 10.6 (brs,1H), 8.17 (d,1H), 7.68 -2 NC 2 H 4 OMe Me CF 3 10.6 (brs, 1H), 8.17 (d, 1H), 7.68
(d,1H), 4.69 (t,2H), 3.85 (t,2H), 3.36 (s,3H), 2.84 (s,3H)-3 N C2H4OMe iPr CF3 (d, 1H), 4.69 (t, 2H), 3.85 (t, 2H), 3.36 (s, 3H), 2.84 (s, 3H) -3 NC 2 H 4 OMe iPr CF 3
-4 CH C2H4OMe CH2OMe CF3 -4 CH C 2 H 4 OMe CH 2 OMe CF 3
-5 N C2H OMe CH2OMe CF3 11.8 (brs,1H), 8.34 (d,1H), 8.02 -5 NC 2 H OMe CH 2 OMe CF 3 11.8 (brs, 1H), 8.34 (d, 1H), 8.02
(d,1H), 4.78 (s,2H), 4.51 (t,2H), 3.77 (t,2H), 3.28 (s,3H), 3.23 (s,3H) (d, 1H), 4.78 (s, 2H), 4.51 (t, 2H), 3.77 (t, 2H), 3.28 (s, 3H), 3.23 (s, 3H)
-6 N C2H OMe CH2OEt CF3 -6 NC 2 H OMe CH 2 OEt CF 3
-7 N C2H OMe CH2OiPr CF3 -7 NC 2 H OMe CH 2 OiPr CF 3
-8 CH C2H OMe CH20(CH2)2OMe CF3 -8 CH C 2 H OMe CH 2 O (CH 2 ) 2 OMe CF 3
-9 N C2H OMe CH20(CH2)2OMe CF3 -9 NC 2 H OMe CH 2 0 (CH 2 ) 2 OMe CF 3
-10 N C2H OMe CH20(CH2)3OMe CF3 -10 NC 2 H OMe CH 2 0 (CH 2 ) 3 OMe CF 3
-11 N C2H OMe CH2OCH2CF3 CF3 -11 NC 2 H OMe CH 2 OCH 2 CF 3 CF 3
-12 N C2H OMe CH2OCH2cPr CF3 -12 NC 2 H OMe CH 2 OCH 2 cPr CF 3
-13 N C2H OMe CH2(3-Me-imidazo- CF3 -13 NC 2 H OMe CH 2 (3-Me-imidazo-CF 3
lin-2-on-1-yl) Nr. B R X Z Physikalische Daten lin-2-on-1-yl) No. BRXZ Physical Data
( H-NMR, DMSO-d6,400 MHz) -14 N C2H4OMe CH2(3-Methoxy-4- CF3 12.17 (brs,1H), 8.24 (d,1H), methyl-1,2,4- 7.77 (d,1H), 5.28 (s,2H), 4.73 triazolin-5-on-1-yl) (t,2H), 4.05 (s,3H), 3.78 (t,2H), (H-NMR, DMSO-d 6 , 400 MHz) -14 NC 2 H 4 OMe CH 2 (3-methoxy-4-CF 3 12.17 (brs, 1H), 8.24 (d, 1H), methyl-1,2 , 4-7.77 (d, 1H), 5.28 (s, 2H), 4.73 triazolin-5-one-1-yl) (t, 2H), 4.05 (s, 3H), 3.78 (t, 2H),
3.27 (s,3H), 3.12 (s,3H) -15 N C2H4OMe CH2SMe CF3 3.27 (s, 3H), 3.12 (s, 3H) -15 NC 2 H 4 OMe CH 2 SMe CF 3
-16 CH C2H4OMe Cl CF3 -16 CH C 2 H 4 OMe Cl CF 3
-17 N C2H4OMe Cl CF3 11.99 (brs,1H), 8.55 (brs,1H), -17 NC 2 H 4 OMe Cl CF 3 11.99 (brs, 1H), 8.55 (brs, 1H),
8.20 (brs,1H), 4.37 (m,2H), 3.72 (m,2H), 2.39 (s,3H) 8.20 (brs, 1H), 4.37 (m, 2H), 3.72 (m, 2H), 2.39 (s, 3H)
-18 N C2H OMe Br CF3 -18 NC 2 H OMe Br CF 3
-19 N C2H OMe Br CF3 -19 NC 2 H OMe Br CF 3
-20 N C2H OMe SMe CF3 8.37 (d,1H), 7.62 (d,1H), 4.59 -20 NC 2 H OMe SMe CF 3 8.37 (d, 1H), 7.62 (d, 1H), 4.59
(m,2H), 3.78 (m,2H), 3.23 (s,3H), (m, 2H), 3.78 (m, 2H), 3.23 (s, 3H),
-21 N C2H OMe F F-21 NC 2 H OMe FF
-22 N C2H OMe F F-22 NC 2 H OMe FF
-23 CH C2H OMe Cl Cl-23 CH C 2 H OMe Cl Cl
-24 N C2H OMe Cl Cl 9.95 (bs,1H), 8.16 (d,1H), 7.46 -24 NC 2 H OMe Cl Cl 9.95 (bs, 1H), 8.16 (d, 1H), 7.46
(d,1H), 4.61 (t,2H), 3.83 (t,2H), 3.39 (s,3H) (d, 1H), 4.61 (t, 2H), 3.83 (t, 2H), 3.39 (s, 3H)
-25 CH C2H OMe Me Cl-25 CH C 2 H OMe Me Cl
-26 N C2H OMe Me Cl-26 NC 2 H OMe Me Cl
-27 N C2H OMe SMe Cl-27 NC 2 H OMe SMe Cl
-28 N C2H OMe S02Me Cl-28 NC 2 H OMe S0 2 Me Cl
-29 CH C2H OMe Cl SMe-29 CH C 2 H OMe Cl SMe
-30 N C2H OMe Cl SMe-30 NC 2 H OMe Cl SMe
-31 CH C2H OMe Me S02Me-31 CH C 2 H OMe Me S0 2 Me
-32 N C2H OMe Me S02Me-32 NC 2 H OMe Me S0 2 Me
-33 N C2H OMe SMe SMe-33 NC 2 H OMe SMe SMe
-34 N C2H OMe S02Me S02Me -34 NC 2 H OMe S0 2 Me S0 2 Me
Formulierungsbeispiele formulation Examples
Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert. A dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem
Figure imgf000058_0001
man 25 Gewichtsteile einer Verbindung der Formel (I) und/oder deren Salze, 64 A readily dispersible, water-wettable powder is obtained by:
Figure imgf000058_0001
25 parts by weight of a compound of the formula (I) and / or salts thereof, 64
Gew.-Teile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaunnsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt. Parts by weight of kaolin-containing quartz as inert material, 10 parts by weight potassium lignosulfonate and 1 part by weight of oleoylmethyltalonic acid sodium as wetting and dispersing agent and ground in a pin mill.
) Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze mit 6 Gew.-Teilen Alkylphenolpolyglykolether (©Triton X 207), 3 Gew.-Teilen A dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (© Triton X 207), 3 parts by weight
Isotridecanolpolyglykolether (8 EO) und 71 Gew.-Teilen paraffinischem  Isotridecanol polyglycol ether (8 EO) and 71 parts by weight paraffinic
Mineralöl (Siedebereich z.B. ca. 255 bis über 277 C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt.  Mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns.
) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew.-Teilen einer ) An emulsifiable concentrate is obtained from 15 parts by weight of a
Verbindung der Formel (I) und/oder deren Salze, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertes Nonylphenol als Emulgator.  Compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
) Ein in Wasser dispergierbares Granulat wird erhalten indem man ) A water-dispersible granules are obtained by
75 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze,  75 parts by weight of a compound of the formula (I) and / or salts thereof,
10 Gew.-Teile ligninsulfonsaures Calcium,  10 parts by weight of lignosulfonic acid calcium,
5 Gew.-Teile Natriumlaurylsulfat,  5 parts by weight of sodium lauryl sulfate,
3 Gew.-Teile Polyvinylalkohol und  3 parts by weight of polyvinyl alcohol and
7 Gew.-Teile Kaolin  7 parts by weight kaolin
mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert.  milled, ground on a pin mill and granulated the powder in a fluidized bed by spraying water as Granulierflüssigkeit.
Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man A water-dispersible granule is also obtained by
25 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze,  25 parts by weight of a compound of the formula (I) and / or salts thereof,
5 Gew.-Teile 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium  5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonate sodium
2 Gew.-Teile oleoylmethyltaunnsaures Natrium,  2 parts by weight of oleoylmethyltaucous sodium,
1 Gew.-Teil Polyvinylalkohol,  1 part by weight of polyvinyl alcohol,
17 Gew.-Teile Calciumcarbonat und  17 parts by weight of calcium carbonate and
50 Gew.-Teile Wasser  50 parts by weight of water
auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet. C. Biologische Beispiele Homogenized on a colloid mill and pre-crushed, then grinded on a bead mill and the suspension thus obtained in a spray tower by means of a Einstoffdüse atomized and dried. C. Biological examples
1 . Herbizide Wirkung gegen Schadpflanzen im Vorauflauf  1 . Herbicidal action against weevils in pre-emergence
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in  Seeds of monocotyledonous or dicotyledonous weeds are cultivated in
Holzfasertöpfen in sandiger Lehmerde ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Wood fiber pots laid in sandy loam soil and covered with soil. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha unter Zusatz von 0,2% Netzmittel auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung werden die Töpfe im Gewächshaus aufgestellt und unter guten Emulsion with a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied to the surface of the cover soil. After the treatment, the pots are placed in the greenhouse and under good
Wachstumsbedingungen für die Testpflanzen gehalten. Die visuelle Bonitur der Schäden an den Versuchspflanzen erfolgt nach einer Versuchszeit von 3 Wochen im Vergleich zu unbehandelten Kontrollen (herbizide Wirkung in Prozent (%): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen). Dabei zeigen beispielsweise die Verbindungen Nr. 1 -16, 1 -44, 1 -60, 1 -125, 1 -154, 1 -162, 1 - 163, 1 -174, 1 -187, 1 -191 , 1 -197, 1 -200, 1 -204, 1 -215, 1 -245, 1 -246, 1 -248, 1 -343, 1 - 345, 1 -361 , 1 -366, 1 -368, 1 -417, 1 -450, 1 -452, 1 -453, 1 -456, 1 -458, 1 -460, 1 -463, 1 - 464, 1 -465, 1 -468, 1 -475, 1 -476, 1 -488, 1 -494, 1 -517, 1 -572, 1 -583, 2-2, 2-4, 2-5, 2-6, 2-7, 2-19, 3-2 und 3-16 bei einer Aufwandmenge von 320 g/ha jeweils eine mindestens 90%-ige Wirkung gegen Abutilon theophrasti, Amaranthus retroflexus, Matricara inodora, Stellaria media, Veronica persica und Viola tricolor. Maintained growth conditions for the test plants. The visual assessment of the damage to the test plants is carried out after a test period of 3 weeks in comparison to untreated controls (herbicidal action in percent (%): 100% effect = plants are dead, 0% effect = like control plants). Here, for example, the compounds Nos. 1-16, 1-44, 1-60, 1-125, 1-154, 1-162, 1-163, 1-174, 1-187, 1-191, 1-197 show , 1-200, 1-204, 1-215, 1-245, 1-246, 1-248, 1-343, 1-345, 1-361, 1-366, 1-368, 1-417, 1 -450, 1-452, 1-453, 1-456, 1-458, 1-460, 1-463, 1-464, 1-465, 1-468, 1-475, 1-476, 1-488 , 1 -494, 1-517, 1-572, 1-583, 2-2, 2-4, 2-5, 2-6, 2-7, 2-19, 3-2 and 3-16 at one Application rate of 320 g / ha each having at least 90% action against Abutilon theophrasti, Amaranthus retroflexus, Matricara inodora, Stellaria media, Veronica persica and Viola tricolor.
2. Herbizide Wirkung gegen Schadpflanzen im Nachauflauf 2. Herbicidal action against harmful plants in postemergence
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen werden in Seeds of monocotyledonous or dicotyledonous weeds are cultivated in
Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und imWood fiber pots laid out in sandy clay soil, covered with soil and in the
Gewächshaus unter guten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat werden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha unter Zusatz von 0,2% Netzmittel auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus unter optimalen Emulsion sprayed with an amount of water equivalent of 600 to 800 l / ha with the addition of 0.2% wetting agent on the green plant parts. After about 3 weeks life of the test plants in the greenhouse under optimal
Wachstumsbedingungen wird die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert (herbizide Wirkung in Prozent (%): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen). Dabei zeigen beispielsweise die Verbindungen Nr.1-23, 1-44, 1-125, 1-128, 1-154, 1-157, 1-162, 1- 188, 1-197, 1-200, 1-215, 1-220, 1-245, 1-246, 1-344, 1-345, 1-350, 1-366, 1-368, 1- 417, 1-450, 1-453, 1-456, 1-460, 1-465, 1-468, 1-475, 1-487, 1-488, 1-494, 1-517, 1- 518, 1 -583, 2-2, 2-4, 2-5, 2-6, 2-19, 3-2, 3-5 und 3-23 bei einer Aufwandmenge von 80 g/ha jeweils eine mindestens 90%-ige Wirkung gegen Abutilon theophrasti, Mathcara inodora, Pharbitis purpureum, Stellaria media, Veronica persica und Viola tricolor. Growth conditions, the effect of the preparations is scored visually compared to untreated controls (herbicidal action in percent (%): 100% effect logo CNRS logo INIST Plants have died, 0% effect = like control plants). For example, Compounds Nos. 1-23, 1-44, 1-125, 1-128, 1-154, 1-157, 1-162, 1-188, 1-197, 1-200, 1-215 , 1-220, 1-245, 1-246, 1-344, 1-345, 1-350, 1-366, 1-368, 1-417, 1-450, 1-453, 1-456, 1 460, 1-465, 1-468, 1-475, 1-487, 1-488, 1-494, 1-517, 1-518, 1-583, 2-2, 2-4, 2-5 , 2-6, 2-19, 3-2, 3-5 and 3-23 at an application rate of 80 g / ha each have at least 90% activity against Abutilon theophrasti, Mathcara inodora, Pharbitis purpureum, Stellaria media, Veronica persica and viola tricolor.

Claims

Patentansprüche claims
1 . N-(Tetrazol-5-yl)- und N-(Thazol-5-yl)arylcarbonsäureamide der Formel (I) oder deren Salze 1 . N- (tetrazol-5-yl) - and N- (thazol-5-yl) arylcarboxamides of the formula (I) or salts thereof
Figure imgf000062_0001
Figure imgf000062_0001
worin wherein
A bedeutet N oder CY, B bedeutet N oder CH, A is N or CY, B is N or CH,
X bedeutet Nitro, Halogen, Cyano, Formyl, Rhodano, (Ci-C6)-Alkyl, Halogen-(Ci- C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)- alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)NR1OR1, OR1, OCOR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)- Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)- Alkyl-SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl- NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, NR1R2, P(O)(OR5)2, CH2P(O)(OR5)2, (Ci-C6)- Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die beiden letztgenannten Reste jeweils durch s Reste Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)- Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, und wobei Heterocyclyl n Oxogruppen trägt, X is nitro, halogen, cyano, formyl, thiocyanato, (Ci-C6) alkyl, halo (Ci- C6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl , (C2-C6) alkynyl, halo (C 3 -C 6) - alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O) N (R 1 ) 2 , OC (O) N (R 1 ) 2 , C (O) NR 1 OR 1 , OR 1 , OCOR 1 , OSO 2 R 2 , S ( O) n R 2 , SO 2 OR 1 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -alkyl-CO 2 R 1 , ( Ci-C 6) - alkyl-SO 2 OR 1, (Ci-C 6) alkyl-CON (R 1) 2, (Ci-C 6) alkyl-SO 2 N (R 1) 2, (Ci- C 6 ) -Alkyl- NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , NR 1 R 2 , P (O) (OR 5 ) 2 , CH 2 P (O) (OR 5 ) 2 , (C 1 -C 6) -alkyl heteroaryl, (C 1 -C 6) -alkyl heterocyclyl, where the last two radicals are each represented by s radicals halogen, (C 1 -C 6) -alkyl, Halogeno (C 1 -C 6) -alkyl, S (O) n - (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy, halogeno (C 1 -C 6) -alkoxy, and where heterocyclyl carries n oxo groups,
Y bedeutet Wasserstoff, Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2- C6)-alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR1, Y is hydrogen, nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, or halogen- (C 2 -C 6 ) -alkenyl , (C 2 -C 6 ) -alkynyl, halogeno (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, halogeno (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl, C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 ,
COOR1,OCOOR1, NR1COOR1, C(O)N(R1)2, NR1C(O)N(R1)2, OC(O)N(R1)2, COOR 1 , OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O) N (R 1 ) 2 , OC (O) N (R 1 ) 2 ,
CO(NOR1)R1, NR1SO2R2, NR1COR1, OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2 (C1- C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)-Alkyl-CN, (Ci-C6)-Alkyl-SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2j (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, N(R1)2, P(O)(OR5)2, CH2P(O)(OR5)2, (Ci-C6)-Alkyl-Phenyl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)- Alkyl-Heterocyclyl, Phenyl, Heteroaryl oder Heterocyclyl, wobei die letzten 6 Reste jeweils durch s Reste aus der Gruppe Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci- C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C4)-alkyl und Cyanonnethyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, CO (NOR 1 ) R 1 , NR 1 SO 2 R 2 , NR 1 COR 1 , OR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2 OR 1 , SO 2 N (R 1 ) 2 (C1- C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -alkyl-CO 2 R 1 , (C 1 -C 6 ) -alkyl-CN, (C 1 -C 6 ) -alkyl-SO 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2j (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , N (R 1 ) 2 , P (O) (OR 5 ) 2 , CH 2 P (O) (OR 5 ) 2 , (C 1 -C 6 ) -alkyl-phenyl, (C 1 -C 6 ) -alkyl-heteroaryl , (C 1 -C 6) -alkyl heterocyclyl, phenyl, heteroaryl or heterocyclyl, where the last 6 radicals are in each case represented by s radicals from the group halogen, nitro, cyano, (C 1 -C 6) -alkyl, halogeno (C 1 -C 4) 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, C 6 ) alkoxy- (C 1 -C 4 ) -alkyl and cyano-nyl, and wherein heterocyclyl carries n oxo groups,
Z bedeutet Halogen, Cyano, Rhodano, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C2-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)- cycloalkyl-(Ci-C6)-alkyl, COR1, COOR1, OCOOR1, NR1COOR1, C(O)N(R1)2, Z represents halogen, cyano, thiocyanato, halo (Ci-C6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halogen - (C 2 -C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, halo (C 3 -C 6) - cycloalkyl- (Ci-C 6) alkyl, COR 1, COOR 1, OCOOR 1, NR 1 COOR 1, C (O) N (R 1) 2,
NR1C(O)N(R1)2, OC(O)N(R1)2, C(O)NR1OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)-Alkyl-SO2OR1, (Ci-C6)-Alkyl- CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, N(R1)2, P(O)(OR5)2, Heteroaryl, Heterocyclyl oder Phenyl, wobei die letzten drei Reste jeweils durch s Reste aus der Gruppe Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy oder Halogen- (Ci-C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, oder Z kann auch Wasserstoff, (Ci-Ce)-Alkyl oder (Ci-Ce)-Alkoxy bedeuten, falls Y für den Rest S(O)nR2 steht, NR 1 C (O) N (R 1 ) 2 , OC (O) N (R 1 ) 2 , C (O) NR 1 OR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2 OR 1 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -alkyl-CO 2 R 1 , (C 1 -C 6 ) -alkyl- SO 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , N (R 1 ) 2 , P (O) (OR 5 ) 2 , heteroaryl, heterocyclyl or phenyl, where the last three radicals are each represented by s Radicals from the group halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - (C 1 -C 6 ) Alkyl, (C 1 -C 6) -alkoxy or halogeno (C 1 -C 6) -alkoxy, and where heterocyclyl carries n oxo groups, or Z can also be hydrogen, (C 1 -C 6) -alkyl or (C 1 -C 4) - Alkoxy, if Y is the radical S (O) n R 2 ,
R bedeutet CH2R6, R is CH 2 R 6 ,
durch m Oxogruppen substituiertes CH2-Heterocyclyl, by m oxo groups substituted CH 2 heterocyclyl,
durch t (Ci-C6)-Alkylgruppen substituiertes (C3-C7)-Cycloalkyl, (C 3 -C 7) -cycloalkyl substituted by t (C 1 -C 6) -alkyl groups,
jeweils durch u Reste aus der Gruppe bestehend aus Nitro, Cyano, Hydroxy, Oxo, SiR5 3, PO(OR5)2, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, N(R3)2, COR3, OCOR3, NR3COR3, NR3SO2R4, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl substituiertes (C2-C6)- Alkyl, (C3-C7)-Cycloalkyl, Halogen-(C2-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl oder Halogen-(C2-C6)-alkinyl, wobei die Reste (C3-C6)- Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl jeweils durch s Substituenten aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Cyano, Nitro, Trifluormethyl und Halogen substituiert sind, und wobei Heterocyclyl und Cycloalkyl n Oxogruppen tragen, in each case by u radicals from the group consisting of nitro, cyano, hydroxyl, oxo, SiR 5 3 , PO (OR 5 ) 2 , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - alkoxy, halo (Ci-C 6) -alkoxy, N (R 3) 2, COR 3, OCOR 3, NR 3 COR 3, NR 3 SO 2 R 4, (C 3 -C 6) -cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl substituted (C 2 -C 6) - alkyl, (C 3 -C 7) cycloalkyl, halo (C 2 -C 6) alkyl , (C 2 -C 6) alkenyl, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl or halo (C 2 -C 6) -alkynyl, where the radicals (C3-C6 ) - Cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each substituted by s substituents selected from the group consisting of methyl, ethyl, methoxy, cyano, nitro, trifluoromethyl and halo, and wherein Heterocyclyl and cycloalkyl carry n oxo groups,
Q bedeutet O, S oder NR3, Q is O, S or NR 3 ,
R1 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2- C6)-Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3- C6)-Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocycl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)- Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR3-Heteroaryl, (Ci-C6)-Alkyl-NR3-Heterocyclyl wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3,R 1 represents hydrogen, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C2-C6) alkenyl, (C 2 - C 6) haloalkenyl, (C2-C6) alkynyl , (C2-C6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 - C 6) cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) alkyl- heteroaryl , Heterocycl, (Ci-C 6) alkyl-heterocyclyl, (Ci-C 6) alkyl-O-heteroaryl, (Ci-C 6) - alkyl-O-heterocyclyl, (Ci-C 6) alkyl-NR 3- heteroaryl, (C 1 -C 6 ) -alkyl-NR 3 -heterocyclyl where the 21 latter radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, rhodano, OR 3 , S (O) n R 4 , N (R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 ,
SCOR4, NR3COR3, NR3SO2R4' CO2R3, COSR4, CON(R3)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, SCOR 4 , NR 3 COR 3 , NR 3 SO 2 R 4 'CO 2 R 3 , COSR 4 , CON (R 3 ) 2 and (C 1 -C 4 ) alkoxy- (C 2 -C 6 ) alkoxycarbonyl and wherein heterocyclyl carries n oxo groups,
R2 bedeutet (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (C2-C6)-Alkenyl, (C2-C6)- Halogenalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkenyl, (C3-C6)-Halogencycloalkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-Ce)-Alkyl- Heteroaryl, Heterocyclyl, (Ci-C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci- C6)-Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR3-Heteroaryl, (Ci-C6)-Alkyl-NR3-Heterocyclyl wobei die 21 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, Rhodano, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, SCOR4, NR3COR3, NR3SO2R4, CO2R3, COSR4, CON(R3)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R3 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, R 2 is (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) - haloalkenyl, (C 2 -C 6) alkynyl , (C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C 3 -C 6) - cycloalkenyl, (C3-C 6) halocycloalkyl, (Ci-C6) alkyl-O- ( Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, phenyl, phenyl (Ci-C 6) alkyl, heteroaryl, (Ci-Ce) alkyl Heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 6 ) -alkyl- NR 3 heteroaryl, (C 1 -C 6 ) -alkyl-NR 3 -heterocyclyl where the 21 latter radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, rhodano, OR 3 , S (O) n R 4 , N (R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , SCOR 4 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , COSR 4 , CON (R 3 ) 2 and (Ci -C 4) alkoxy (C 2 -C 6) - alkoxycarbonyl are substituted, and wherein heterocyclyl carries n oxo groups, R 3 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) Cycloalkyl or (C 3 -C 6) -cycloalkyl- (C 1 -C 6) -alkyl,
R4 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl oder (C2-C6)-Alkinyl, (C3-C6)-Cycloalkyl oder (C3-C6)-Cycloal kyl-(Ci -C6)-al kyl , bedeutet (Ci-C )-Alkyl, R 4 is (Ci-C 6) -alkyl, (C 2 -C 6) -alkenyl or (C 2 -C 6) -alkynyl, (C3-C6) -cycloalkyl or (C3-C 6) alkyl -Cycloal - (C 1 -C 6 ) -alcyl, represents (C 1 -C 4) -alkyl,
R6 bedeutet OCOOR4, NR4COOR4, S(O)n-(Ci-C6)-Alkyl, S(O)n-(Ci-C6)-Haloalkyl, Nitro, Cyano, SiR53, PO(OR5)2, Heterocyclyl oder Cycloalkyl, wobei die beiden letztgenannten Reste m Oxo- oder Hydroxygruppen tragen, bedeutet 1 oder 2, R 6 is OCOOR 4 , NR 4 COOR 4 , S (O) n - (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -haloalkyl, nitro, cyano, SiR 5 3, PO (OR 5 ) 2, heterocyclyl or cycloalkyl, where the last two radicals m bear oxo or hydroxyl groups, 1 or 2,
bedeutet 0, 1 oder 2,  means 0, 1 or 2,
bedeutet 0, 1 , 2 oder 3,  means 0, 1, 2 or 3,
bedeutet 1 , 2, 3 oder 4,  means 1, 2, 3 or 4,
bedeutet 1 , 2, 3, 4 oder 5.  means 1, 2, 3, 4 or 5.
N-(Tetrazol-5-yl)- und N-(Triazol-5-yl)arylcarbonsäureamide nach Anspruch 1 , bedeutet N oder CY, N- (tetrazol-5-yl) and N- (triazol-5-yl) arylcarboxamides according to claim 1, N or CY,
B bedeutet N oder CH, B is N or CH,
X bedeutet Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3- C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR1, OR1, OCOR1, OSO2R2, S(O)nR2, SO2OR1 , SO2N(R1)2, NR1SO2R2, NR1COR1, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)-Alkyl-SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl- NR1COR1 oder (Ci-C6)-Alkyl-NR1SO2R2, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl- Heterocyclyl, wobei die beiden letztgenannten Reste jeweils durch s Reste Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci- C6)-alkoxy substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, X is nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogeno (C 2 -C 6 ) -alkenyl, (C 2 -C 4 ) -alkenyl -C 6) alkynyl, halo (C3-C6) -alkynyl, (C 3 - C 6) cycloalkyl, halo (C3-C6) cycloalkyl, Ci-C6) alkyl-O- (C -C 6) alkyl, (C 3 -C 6) - cycloalkyl, (Ci-C 6) alkyl, halo (C3-C6) cycloalkyl- (Ci-C 6) alkyl, COR 1, OR 1 , OCOR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2OR 1 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -Alkyl-CO 2 R 1 , (C 1 -C 6 ) -alkyl-SO 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 or (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 ) -alkyl heteroaryl, (Ci C 6 ) alkyl heterocyclyl, where the last two radicals are each represented by s radicals halogen, (Ci-C 6 ) alkyl, halogeno (Ci-C 6 ) alkyl, S (O) n - (Ci-C 6 ) alkyl, (C 1 -C 6 ) alkoxy, halo (C 1 -C 6) alkoxy, and wherein i carries heterocyclyl n oxo groups,
Y bedeutet Wasserstoff, Nitro, Halogen, Cyano, Rhodano, (Ci-C6)-Alkyl, Halogen- (Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3- C6)-alkinyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkenyl, Halogen-(C3-C6)-cycloalkyl, (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)-cycloalkyl-(Ci-C6)-alkyl, COR1, OR1, COOR1, OSO2R2, S(O)nR2, SO2OR1, SO2 N(R1)2, N(R1)2, NR1SO2R2, NR1COR1, (C1- C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)-Alkyl-SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl- SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, (Ci-C6)-Alkyl-Phenyl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, Phenyl, Heteroaryl oder Y is hydrogen, nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, or halogen- (C 2 -C 6 ) -alkenyl , (C 2 -C 6 ) -alkynyl, halogen- (C 3 - C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkenyl, halogeno (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogen- (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , OR 1 , COOR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2OR 1 , SO 2 N (R 1 ) 2 , N (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -alkyl-CO 2 R 1 , (C 1 -C 6 ) -alkyl-SO 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl, -SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , ( C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 ) -alkyl-phenyl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) -alkyl-heterocyclyl, phenyl, heteroaryl or
Heterocyclyl, wobei die sechs letztgenannten Reste jeweils durch s Reste aus der Gruppe Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)- Alkoxy-(Ci-C4)-alkyl und Cyanomethyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Heterocyclyl, where the six last-mentioned radicals each substituted by s radicals selected from the group halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, S (O) n - (Ci-C 6) -alkyl, (Ci-Ce) alkoxy, halo (Ci-C 6) alkoxy, (Ci-C6) - alkoxy- (Ci-C4) - substituted alkyl and cyanomethyl, and wherein heterocyclyl n carries oxo groups,
Z bedeutet Halogen, Cyano, Rhodano, Halogen-(Ci-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)-alkenyl, (C2-C6)-Alkinyl, Halogen-(C3-C6)-alkinyl, (C3-C6)-Cycloalkyl, Halogen-(C3-C6)-cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, Halogen-(C3-C6)- cycloalkyl-(Ci-C6)-alkyl, COR1, COOR1, C(O)N(R1)2, C(O)NR1OR1, OSO2R2, S(O)nR2, SO2OR1, SO2N(R1)2, NR1SO2R2, NR1COR1, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl-OCOR1, (Ci-C6)-Alkyl-OSO2R2, (Ci-C6)-Alkyl-CO2R1, (Ci-C6)-Alkyl- SO2OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, 1 ,2,4-Triazol-1 -yl, oder Z represents halogen, cyano, thiocyanato, halo (Ci-C6) alkyl, (C2-C6) alkenyl, halo (C2-C6) alkenyl, (C2-C6) alkynyl, halo (C3 -C 6) -alkynyl, (C3-C6) cycloalkyl, halo (C3-C6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, halo (C 3 - C 6 ) - cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR 1 , C (O) N (R 1 ) 2 , C (O) NR 1 OR 1 , OSO 2 R 2 , S (O) n R 2 , SO 2 OR 1 , SO 2 N (R 1 ) 2 , NR 1 SO 2 R 2 , NR 1 COR 1 , (C 1 -C 6 ) -alkyl-S (O) n R 2 , (C 1 -C 6 ) - Alkyl-OR 1 , (C 1 -C 6 ) -alkyl-OCOR 1 , (C 1 -C 6 ) -alkyl-OSO 2 R 2 , (C 1 -C 6 ) -alkyl-CO 2 R 1 , (C 1 -C 6 ) -Alkyl-SO 2 OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , 1, 2,4-triazol-1-yl, or
Z kann auch Wasserstoff, (Ci-Ce)-Alkyl oder (Ci-Ce)-Alkoxy bedeuten, falls Y für den Rest S(O)nR2 steht, R bedeutet CH2R6, Z can also be hydrogen, (C 1 -C 6) -alkyl or (C 1 -C 6) -alkoxy, if Y is the radical S (O) n R 2 , R is CH 2 R 6 ,
durch m Oxogruppen substituiertes CH2-Heterocyclyl, by oxo-substituted CH 2 heterocyclyl,
jeweils durch u Reste aus der Gruppe bestehend aus Nitro, Cyano, Hydroxy, Oxo, SiR5 3, PO(OR5)2, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, N(R3)2, COR3, OCOR3, NR3COR3, NR3SO2R4, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl substituiertes (C2-C6)- Alkyl, (C3-C7)-Cycloalkyl, Halogen-(C2-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl oder Halogen-(C2-C6)-alkinyl, wobei die Reste (C3-C6)- Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl jeweils durch s Substituenten aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Cyano, Nitro, Trifluormethyl und Halogen substituiert sind, und wobei Heterocyclyl und Cycloalkyl n Oxogruppen tragen, in each case by u radicals from the group consisting of nitro, cyano, hydroxyl, oxo, SiR 5 3 , PO (OR 5 ) 2 , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - alkoxy, halo (Ci-C 6) -alkoxy, N (R 3) 2, COR 3, OCOR 3, NR 3 COR 3, NR 3 SO 2 R 4, (C 3 -C 6) -cycloalkyl, heteroaryl, Heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl substituted (C 2 -C 6 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, halo (C 2 -C 6 ) -alkyl, ( C 2 -C 6 ) alkenyl, halogeno (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl or halo (C 2 -C 6 ) alkynyl, where the radicals (C 3 -C 6 ) -cycloalkyl, heteroaryl , Heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each represented by s substituents from the group consisting of methyl, Substituted ethyl, methoxy, cyano, nitro, trifluoromethyl and halogen, and wherein heterocyclyl and cycloalkyl carry n oxo groups,
Q bedeutet O, S oder NR3, Q is O, S or NR 3 ,
R1 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci-Ce)-Alkyl- Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci-Ce)-Alkyl- NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei die 16 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, NR3COR3, NR3SO2R4, CO2R3, CON(R3)2 und (Ci-C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 1 represents hydrogen, (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) - cycloalkyl, (C3-C6) cycloalkyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) - Alkyl-heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl-heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 4) -alkyl- NR 3 heteroaryl or (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, where the last-mentioned radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, OR 3 , S (O) n R 4 , N ( R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , CON (R 3 ) 2 and (C 1 -C 4 ) -alkoxy- C 2 -C 6) alkoxycarbonyl are substituted, and wherein heterocyclyl n carries oxo groups,
R2 bedeutet (Ci -C6)-Al kyl , (C2-C6)-Al kenyl , (C2-C6)-Al kinyl , (C3-C6)-Cycloal kyl , (C3- C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-Ce)- alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (C1 -C6)-Alkyl-Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (C1 -C6)-Alkyl-O-Heterocyclyl, (Ci-C6)-Alkyl-NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei diese Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, NR3SO2R4, COR3, OCOR3, NR3COR3, CO2R3, CON(R3)2 und (Ci-C4)-Alkoxy-(C2-C6)- alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R3 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Al kenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, R 2 is (Ci-C6) -alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkyl kinyl, (C 3 -C 6) -Cycloal alkyl, (C 3 - C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 4) -alkyl C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 6 ) -Alkyl-NR 3 -heteroaryl or (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, where these radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, OR 3 , S (O) n R 4 , N (R 3 ) 2 , NR 3 OR 3 , NR 3 SO 2 R 4 , COR 3 , OCOR 3 , NR 3 COR 3 , CO 2 R 3 , CON (R 3 ) 2 and (C 1 -C 4 ) alkoxy - (C 2 -C 6 ) alkoxycarbonyl substituted, and wherein heterocyclyl n carries oxo groups, R 3 is hydrogen, (Ci-C 6 ) alkyl, (C 2 -C 6 ) -Al kenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) - cycloalkyl or (C3-C6) cycloalkyl (Ci-C 6) alkyl,
R4 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Al kenyl oder (C2-C6)-Al kinyl, R5 bedeutet Methyl oder Ethyl, R 4 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl or (C 2 -C 6 ) -alkynyl, R 5 is methyl or ethyl,
R6 bedeutet OCOOR4, NR4COOR4, S(O)n-(Ci-C6)-Alkyl, S(O)n-(Ci-C6)-Haloalkyl, Nitro, Cyano, SiR53, PO(OR5)2 oder Heterocyclyl, das m Oxogruppen trägt, m bedeutet 1 oder 2, R 6 is OCOOR 4 , NR 4 COOR 4 , S (O) n - (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -haloalkyl, nitro, cyano, SiR 5 3, PO (OR 5 ) 2 or heterocyclyl bearing m oxo groups, m is 1 or 2,
n bedeutet 0, 1 oder 2, n is 0, 1 or 2,
s bedeutet 0, 1 , 2 oder 3, s is 0, 1, 2 or 3,
u bedeutet 1 , u is 1,
2, 3, 4 oder 5. 2, 3, 4 or 5.
3. N-(Tetrazol-5-yl)- und N-(Triazol-5-yl)arylcarbonsäureamide nach Anspruch 1 oder 2, worin 3. N- (tetrazol-5-yl) - and N- (triazol-5-yl) arylcarbonsäureamide according to claim 1 or 2, wherein
A bedeutet N oder CY,  A is N or CY,
B bedeutet N oder CH, B is N or CH,
X bedeutet Nitro, Halogen, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, (C3-C6)- Cycloalkyl, OR1, S(O)nR2, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)-Alkyl-OR1, (Ci-C6)-Alkyl- CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl-Heterocyclyl, wobei die beiden letztgenannten Reste jeweils durch s Reste Halogen, (Ci-C6)-Alkyl, Halogen-(Ci-C6)-alkyl, S(O)n-(Ci- C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy substituiert sind, und wobei X is nitro, halo, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) - cycloalkyl, OR 1, S (O) n R 2 ( C 1 -C 6 -alkyl-S (O) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) Alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) -alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 ) -alkyl Heteroaryl, (C 1 -C 6) -alkyl heterocyclyl, where the last two radicals are each represented by s radicals halogen, (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkyl, S (O) n - ( C 6) alkyl, (C 1 -C 6) alkoxy, halo (C 1 -C 6) alkoxy, and wherein
Heterocyclyl n Oxogruppen trägt, Heterocyclyl carries n oxo groups,
Y Wasserstoff, Nitro, Halogen, Cyano, (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, OR1, S(O)nR2, SO2N(R1)2, N(R1)2, NR1SO2R2, NR1COR1, (Ci-C6)-Alkyl-S(O)nR2, (Ci-C6)- Alkyl-OR1, (Ci-C6)-Alkyl-CON(R1)2, (Ci-C6)-Alkyl-SO2N(R1)2, (Ci-C6)-Alkyl-NR1COR1, (Ci-C6)-Alkyl-NR1SO2R2, (Ci-C6)-Alkyl-Phenyl, (Ci-C6)-Alkyl-Heteroaryl, (Ci-C6)-Alkyl- Heterocyclyl, Phenyl, Heteroaryl oder Heterocyclyl, wobei die letzten 6 Reste jeweils durch s Reste aus der Gruppe Halogen, Nitro, Cyano, (Ci-C6)-Alkyl, Halogen-(Ci-Ce)- alkyl, (C3-C6)-Cycloalkyl, S(O)n-(Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy, Halogen-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxy-(Ci-C4)-alkyl und Cyanonnethyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, Y is hydrogen, nitro, halogen, cyano, (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, OR 1, S (O) n R 2, SO 2 N (R 1) 2, N (R 1) 2, NR 1 SO 2 R 2, NR 1 COR 1, (Ci-C 6) alkyl-S (O) n R 2, (Ci-C 6) - alkyl-OR 1, (Ci-C 6 ) -Alkyl-CON (R 1 ) 2 , (C 1 -C 6 ) -alkyl-SO 2 N (R 1 ) 2 , (C 1 -C 6 ) -alkyl-NR 1 COR 1 , (C 1 -C 6 ) - Alkyl-NR 1 SO 2 R 2 , (C 1 -C 6 ) -alkyl-phenyl, (C 1 -C 6 ) -alkyl-heteroaryl, (C 1 -C 6 ) -alkyl-heterocyclyl, phenyl, heteroaryl or heterocyclyl, where the last 6 radicals in each case by s radicals from the group halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, S (O) n - ( C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 4 ) -alkyl and cyanoethyl, and wherein Heterocyclyl carries n oxo groups,
Z bedeutet Halogen, Cyano, Halogen-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, S(O)nR2, 1 ,2,4-Triazol-1 -yl, oder Z kann auch Wasserstoff, Methyl, Methoxy oder Ethoxy bedeuten, falls Y für den Rest S(O)nR2 steht, R bedeutet CH2R6, Z represents halogen, cyano, halo (Ci-C 6) alkyl, (C3-C6) -cycloalkyl, S (O) n R 2, 1, 2,4-triazol-1-yl, or Z may also be Is hydrogen, methyl, methoxy or ethoxy, if Y is the radical S (O) n R 2 , R is CH 2 R 6 ,
Ch -Heterocyclyl, wobei Heterocyclyl m Oxogruppen trägt,  Ch heterocyclyl, where heterocyclyl carries m oxo groups,
jeweils durch u Reste aus der Gruppe bestehend aus Nitro, Cyano, Hydroxy, Oxo, SiR5 3, PO(OR5)2, S(O)n-(Ci-C6)-Alkyl, (Ci-C6)-Alkoxy, Halogen-(Ci-C6)-alkoxy, N(R3)2, COR3, OCOR3, NR3COR3, NR3SO2R4, (C3-C6)-Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl substituiertes (C2-C6)- Alkyl, (C3-C7)-Cycloalkyl, Halogen-(C2-C6)-alkyl, (C2-C6)-Alkenyl, Halogen-(C2-C6)- alkenyl, (C2-C6)-Alkinyl oder Halogen-(C2-C6)-alkinyl, wobei die Reste (C3-C6)- Cycloalkyl, Heteroaryl, Heterocyclyl, Phenyl, Q-Heteroaryl, Q-Heterocyclyl, Q-Phenyl und Q-Benzyl jeweils durch s Substituenten aus der Gruppe bestehend aus Methyl, Ethyl, Methoxy, Cyano, Nitro, Trifluormethyl und Halogen substituiert sind, und wobei Heterocyclyl und Cycloalkyl n Oxogruppen tragen, in each case by u radicals from the group consisting of nitro, cyano, hydroxyl, oxo, SiR 5 3 , PO (OR 5 ) 2 , S (O) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) - alkoxy, halo (Ci-C 6) -alkoxy, N (R 3) 2, COR 3, OCOR 3, NR 3 COR 3, NR 3 SO 2 R 4, (C 3 -C 6) -cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl substituted (C 2 -C 6) - alkyl, (C 3 -C 7) cycloalkyl, halo (C 2 -C 6) alkyl , (C 2 -C 6) alkenyl, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl or halo (C 2 -C 6) -alkynyl, where the radicals (C3-C6 ) - cycloalkyl, heteroaryl, heterocyclyl, phenyl, Q-heteroaryl, Q-heterocyclyl, Q-phenyl and Q-benzyl are each substituted by s substituents selected from the group consisting of methyl, ethyl, methoxy, cyano, nitro, trifluoromethyl and halogen, and wherein heterocyclyl and cycloalkyl carry n oxo groups,
Q bedeutet O, S oder NR3, Q is O, S or NR 3 ,
R1 bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkyl-O-(Ci-C6)-alkyl, Phenyl, Phenyl-(Ci-C6)-alkyl, Heteroaryl, (Ci-C6)-Alkyl-Heteroaryl, Heterocyclyl, (Ci-Ce)-Alkyl- Heterocyclyl, (Ci-C6)-Alkyl-O-Heteroaryl, (Ci-C6)-Alkyl-O-Heterocyclyl, (Ci-Ce)-Alkyl- NR3-Heteroaryl oder (Ci-C6)-Alkyl-NR3-Heterocyclyl, wobei die 16 letztgenannten Reste durch s Reste aus der Gruppe bestehend aus Cyano, Halogen, Nitro, OR3, S(O)nR4, N(R3)2, NR3OR3, COR3, OCOR3, NR3COR3, NR3SO2R4, CO2R3, CON(R3)2 und (Ci-C4)-Alkoxy-(C2-C6)-alkoxycarbonyl substituiert sind, und wobei Heterocyclyl n Oxogruppen trägt, R 1 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) - Cycloalkyl- (Ci-C 6 ) -alkyl, (Ci-C6) -alkyl-O- (Ci-C 6 ) -alkyl, phenyl, phenyl (Ci-C 6 ) -alkyl, heteroaryl, (Ci-C 6 ) -Alkyl-heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl-heterocyclyl, (C 1 -C 6 ) -alkyl-O-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (C 1 -C 4) - Alkyl-NR 3 -heteroaryl or (C 1 -C 6) -alkyl-NR 3 -heterocyclyl, where the last-mentioned radicals are represented by s radicals from the group consisting of cyano, halogen, nitro, OR 3 , S (O) n R 4 , N (R 3 ) 2 , NR 3 OR 3 , COR 3 , OCOR 3 , NR 3 COR 3 , NR 3 SO 2 R 4 , CO 2 R 3 , CON (R 3 ) 2 and (C 1 -C 4 ) alkoxy - (C 2 -C 6) alkoxycarbonyl are substituted, and wherein heterocyclyl n carries oxo groups,
R2 bedeutet (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl oder (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, wobei diese drei vorstehend genannten Reste jeweils durch s Reste aus der Gruppe bestehend aus Halogen und OR3 substituiert sind, R3 bedeutet Wasserstoff oder (Ci-C6)-Alkyl, bedeutet (Ci-C6)-Alkyl, R 2 is (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, where these three radicals mentioned above are each represented by s radicals from the group consisting of Group consisting of halogen and OR 3 are substituted, R 3 is hydrogen or (C 1 -C 6 ) -alkyl, is (C 1 -C 6 ) -alkyl,
R5 bedeutet Methyl oder Ethyl, R6 bedeutet OCOOR4, NR4COOR4, S(O)n-(Ci-C6)-Alkyl, S(O)n-(Ci-C6)-Haloalkyl, Nitro, Cyano, SiR5 3, PO(OR5)2, m bedeutet 1 oder 2, R 5 is methyl or ethyl, R 6 is OCOOR 4 , NR 4 COOR 4 , S (O) n - (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -haloalkyl, nitro, cyano, SiR 5 3 , PO (OR 5 ) 2 , m is 1 or 2,
n bedeutet 0, 1 oder 2, n is 0, 1 or 2,
s bedeutet 0, 1 , 2 oder 3, s is 0, 1, 2 or 3,
u bedeutet 1 , 2, 3, 4 oder 5. u is 1, 2, 3, 4 or 5.
4. Herbizide Mittel, gekennzeichnet durch einen herbizid wirksamen Gehalt an mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 3. 4. A herbicidal composition, characterized by a herbicidally active content of at least one compound of the formula (I) according to one of claims 1 to 3.
5. Herbizide Mittel nach Anspruch 4 in Mischung mit Formulierungshilfsmitteln. 5. A herbicidal composition according to claim 4 in admixture with formulation auxiliaries.
6. Herbizide Mittel nach Anspruch 4 oder 5 enthaltend mindestens einen weiteren Pestizid wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide, Safener und Wachstumsregulatoren. 6. A herbicidal composition according to claim 4 or 5 containing at least one further pesticide active substance from the group of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
Herbizide Mittel nach Anspruch 6 enthaltend einen Safener. A herbicidal composition according to claim 6 comprising a safener.
8. Herbizide Mittel nach Anspruch 7 enthaltend cyprosulfamid, cloquintocet-mexyl, mefenpyr-diethyl oder isoxadifen-ethyl. 8. A herbicidal composition according to claim 7 containing cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
9. Herbizide Mittel nach einem der Ansprüche 6 bis 8 enthaltend ein weiteres Herbizid. 9. A herbicidal composition according to any one of claims 6 to 8 containing a further herbicide.
10. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge mindestens einer Verbindung der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder eines herbiziden Mittels nach einem der Ansprüche 4 bis 9 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert. 10. A method for controlling unwanted plants, characterized in that an effective amount of at least one compound of formula (I) according to any one of claims 1 to 3 or a herbicidal composition according to any one of claims 4 to 9 on the plants or on the place of unwanted plant growth applied.
1 1 . Verwendung von Verbindungen der Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln nach einem der Ansprüche 4 bis 9 zur Bekämpfung unerwünschter Pflanzen. 1 1. Use of compounds of the formula (I) according to one of Claims 1 to 3 or of herbicidal agents according to one of Claims 4 to 9 for controlling unwanted plants.
12. Verwendung nach Anspruch 1 1 , dadurch gekennzeichnet, daß die 12. Use according to claim 1 1, characterized in that the
Verbindungen der Formel (I) zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden.  Compounds of formula (I) for controlling undesirable plants in crops of crops are used.
13. Verwendung nach Anspruch 12, dadurch gekennzeichnet, daß die Nutzpfl transgene Nutzpflanzen sind. 13. Use according to claim 12, characterized in that the Nutzpfl are transgenic crops.
PCT/EP2012/064863 2011-08-03 2012-07-30 N-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamides and use thereof as herbicides WO2013017559A1 (en)

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JP2014523298A JP6078065B2 (en) 2011-08-03 2012-07-30 N- (tetrazol-5-yl) arylcarboxamides and N- (triazol-5-yl) arylcarboxamides and their use as herbicides
BR112014002191A BR112014002191B1 (en) 2011-08-03 2012-07-30 N- (TETRAZOL-5-IL) - OR N- (TRIAZOL-5-IL) ARYLARBOXYLIC ACID AMIDS, THEIR USE, HERBICIDE COMPOSITION, AND PROCESS FOR COMBATING UNDESIRED PLANTS
US14/233,298 US8822378B2 (en) 2011-08-03 2012-07-30 N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamides and use thereof as herbicides
EP20120745447 EP2739611B1 (en) 2011-08-03 2012-07-30 N-(tetrazol-5-yl)- and n-(triazol-5-yl)aryl carboxamides and their use as hebicides
IN176DEN2014 IN2014DN00176A (en) 2011-08-03 2012-07-30
CN201280038161.9A CN103717581B (en) 2011-08-03 2012-07-30 N-(tetrazolium-5-base) aryl carboxamides and N-(triazole-5-base) aryl carboxamides and the purposes as weedicide thereof
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